吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中的应用转让专利
申请号 : CN201610490135.X
文献号 : CN106070266B
文献日 : 2018-11-30
发明人 : 吴剑 , 徐方舟 , 薛伟 , 宋宝安 , 刘登曰 , 陈吉祥 , 胡德禹 , 杨松
申请人 : 贵州大学
摘要 :
本发明公开了一种吡唑[3,4‑d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中的应用。
权利要求 :
1.一种吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中的应用，所述吡唑[3,4-d]嘧啶酮席夫碱类化合物结构如通式I所示：式中：R选自H，C1-C3的烷基，R1为选自C1-C6的烷基、-N(CH3)2、苯基，取代苯基，芳杂环基；
R2选自甲基、乙基、叔丁基，苯基，取代苯基，芳杂环基；R3可选自H，C1-C3的烷基。
2.如权利要求1所述的吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗烟草花叶病毒、黄瓜花叶病毒、番茄病毒病、辣椒病毒病植物病毒剂中的应用。
3.如权利要求1或2所述的吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗烟草花叶病毒、黄瓜花叶病毒中的应用。
说明书 :
吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中
的应用
技术领域
[0001] 本发明属于农业用抗病毒剂领域，具体来说涉及一种吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中的应用。
背景技术
[0002] 吡唑并[3,4-d]嘧啶酮衍生物具有多种生物，如抗癌活性（Bioorg. Med. Chem., 2011, 6808–6817；Molecules 2014, 19, 3297-3309； Bio. Med. Chem., 2013, 21,
5782-5793；J. Chem. Pharm. Res., 2012, 4, 4097-4106）、杀菌活性（J. Het. Chem.,
2014, 51, 899-905）、抗炎（Sci. Pharmac., 2013, 81, 393-422）、抗心律不齐剂(CN
1036766)等。一些含席夫碱结构的吡唑[3,4-d]嘧啶酮具有良好的抗癌活性（Molecules
2014, 19, 3297-3309；Bio. Med. Chem., 2013, 21, 5782-5793）。但迄今为止，还没有任何报道将含席夫碱结构的吡唑[3,4-d]嘧啶酮类化合物作为抗植物病毒剂应用。
5782-5793；J. Chem. Pharm. Res., 2012, 4, 4097-4106）、杀菌活性（J. Het. Chem.,
2014, 51, 899-905）、抗炎（Sci. Pharmac., 2013, 81, 393-422）、抗心律不齐剂(CN
1036766)等。一些含席夫碱结构的吡唑[3,4-d]嘧啶酮具有良好的抗癌活性（Molecules
2014, 19, 3297-3309；Bio. Med. Chem., 2013, 21, 5782-5793）。但迄今为止，还没有任何报道将含席夫碱结构的吡唑[3,4-d]嘧啶酮类化合物作为抗植物病毒剂应用。
发明内容
[0003] 本发明的目的在于提供的一种吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中的应用。
[0004] 一种吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗烟草花叶病毒、马铃薯Y病毒、马铃薯X病毒、马铃薯S病毒、马铃薯A病毒、黄瓜花叶病毒、番茄病毒病、辣椒病毒病、水稻病毒病等植物病毒剂中的应用。
[0005] 尤其是在抗烟草花叶病毒、黄瓜花叶病毒中的应用。
[0006] 本发明的吡唑[3,4-d]嘧啶酮席夫碱类化合物在制备抗植物病毒剂中的应用，化合物结构如通式I所示：
[0007] I
[0008] 式中：R选自H，C1-C3的烷基，R1为选自C1-C6的烷基、-N(CH3)2、苯基，取代苯基，芳杂环基；R2选自甲基、乙基、叔丁基，苯基，取代苯基，芳杂环基；R3可选自H，C1-C3的烷基。
[0009] 进一步地，通式I所述的化合物中，R选自H，-CH3，R1为选自C1-C3的烷基、-N(CH3)2、苯基，取代苯基，芳杂环基；R2选自甲基、乙基、叔丁基，苯基，取代苯基，芳杂环基；R3可选自H，-CH3，-CH2CH3.
[0010] 更进一步地，通式I所述的化合物中，较为优选的取代基为：
[0011] R选自H，-CH3，R1为选自甲基、乙基、丙基、正丁基、-N(CH3)2、苯基、2-羟基苯基、4-羟基苯基、2氯苯基、3-氯苯基、4-氯苯基、2,4-二氯苯基、2-三氟甲基苯基、4-三氟甲基苯基、对甲氧基苯基、2-氟苯基、3-氟苯基、4-氟苯基、3,4,5-三氟甲基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、2,4-二硝基苯基、2,4-而氟苯基、二乙酰基苯基、3-甲基苯基、4-甲基苯基、2-甲基苯基、呋南-2-基、5-甲基-呋南-2-基、5-溴-呋南-2-基、噻吩-2-基、噻吩-3-基、4-溴-噻吩-2-基、吡啶-4-基、吡啶-3-基、吡啶-2-基、5-溴-吡啶-2-基、5-溴-吡啶-3-基、2-氯吡啶-3-基、咪唑-2-基、吡咯-2-基、3-甲基-4-氯吡唑-2-基、3-甲基噻唑-2-基；R2选自甲基、乙基、叔丁基，苯基，2-氯吡啶基；R3可选自H、-CH3.
[0012]
[0013]
[0014]
[0015]
[0016] 本发明的通式 I 化合物可按照以下合成路线所示的方法进行制备，其中，各个中间体M1、M2及M3可参照文献[Tetrahedron, 1987，43(18), 4195-202]报道的方法进行制备;目标化合物I参照文献Scientia Pharmaceutica, 2013，81(2), 393-422;Molecules, 2014，19(3), 3297-3309； Bioorganic & Medicinal Chemistry, 2011，19(22), 6808-
6817等报道的方法进行制备：
6817等报道的方法进行制备：
[0017]
[0018] 反应式中，中间体及化合物的取代基于上述相同。
[0019] 所合成得到的部分目标化合物核磁数据如下：
[0020] 化合物1：1H NMR (500 MHz, DMSO-d6) δ 9.09 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.55 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.14 (s, 1H, -CH=N), 7.89 (d, J = 7.9 Hz, 2H, benzene-H), 7.59 (d, J = 7.1 Hz, 1H, benzene-H), 7.53 (t, J = 7.5 Hz, 2H, benzene-H), 3.92 (s, 3H, -NCH3); 13C NMR (125 MHz, DMSO-d6) δ 167.43, 154.44, 150.59, 148.43, 135.33, 133.14, 132.91, 129.64,
129.26, 106.00, 34.63.
129.26, 106.00, 34.63.
[0021] 化合物2：1H NMR (500 MHz, Chloroform ) δ 9.27 (s, 1H), 8.19 (s, 1H), 8.15 (s, 1H), 7.96 (s, 1H), 7.51 (s, 1H), 7.32 (s, 1H), 6.92 (d, J = 10.0 Hz,
2H), 3.96 (s, 3H). 13C NMR (125 MHz, Common NMR Solvents ) δ 160.75, 159.91,
156.07, 148.17, 145.11, 136.77, 131.03, 129.68, 121.02, 119.62, 116.26,
85.62, 37.40.
2H), 3.96 (s, 3H). 13C NMR (125 MHz, Common NMR Solvents ) δ 160.75, 159.91,
156.07, 148.17, 145.11, 136.77, 131.03, 129.68, 121.02, 119.62, 116.26,
85.62, 37.40.
[0022] 化合物3：1H NMR (500 MHz, DMSO-d6) δ 10.33 (brs, 1H, -OH), 8.82 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.48 (s, 1H, pyrazolo[3,4-d]pyrimidine-H),
8.11 (s, 1H, -CH=N), 7.73 (s, 1H), 7.72 (s, 1H, benzene-H), 6.89 (s, 1H, benzene-H), 6.88 (s, 1H, benzene-H), 3.90 (s, 3H, -NCH3); 13C NMR (125 MHz, DMSO-d6) δ 168.03, 162.20, 154.41, 150.69, 148.23, 135.17, 131.52, 123.73,
116.48, 106.02, 34.59.
8.11 (s, 1H, -CH=N), 7.73 (s, 1H), 7.72 (s, 1H, benzene-H), 6.89 (s, 1H, benzene-H), 6.88 (s, 1H, benzene-H), 3.90 (s, 3H, -NCH3); 13C NMR (125 MHz, DMSO-d6) δ 168.03, 162.20, 154.41, 150.69, 148.23, 135.17, 131.52, 123.73,
116.48, 106.02, 34.59.
[0023] 化合物4：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.66 (d, J = 15.0 Hz, 2H), 7.15 (s, 1H), 6.85 (d, J = 15.0 Hz, 2H), 5.01 (s, 1H), 3.96 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ 161.04, 159.04, 156.07, 148.17,
145.11, 136.77, 128.87, 126.48, 115.12, 85.62, 37.40.
145.11, 136.77, 128.87, 126.48, 115.12, 85.62, 37.40.
[0024] 化合物5：1H NMR (500 MHz, DMSO-d6 ) δ 8.18 (s, 1H), 8.14 (s, 1H), 7.95 (s, 1H), 7.50 (dd, J = 10.1, 2.1 Hz, 2H), 7.41 (ddd, J = 15.0, 2.0, 1.0 Hz, 1H), 7.26 (ddd, J = 15.0, 9.3, 8.4 Hz, 1H).. 13C NMR (125 MHz, DMSO-d6) δ
165.69, 156.07, 148.17, 145.11, 136.77, 133.23, 130.43, 129.52, 129.18,
129.07, 127.60, 85.62, 37.40.
165.69, 156.07, 148.17, 145.11, 136.77, 133.23, 130.43, 129.52, 129.18,
129.07, 127.60, 85.62, 37.40.
[0025] 化合物6：1H NMR (500 MHz, DMSO-d6 ) δ 8.95 (d, J = 2.9 Hz, 1H), 8.94 (s, 1H), 8.37 (s, 2H), 8.19 (s, 2H), 8.05 (s, 2H), 7.84 (s, 2H), 7.73 (s, 2H), 7.67 – 7.64 (m, 1H), 7.64 (s, 1H), 7.52 (d, J = 30.0 Hz, 4H), 7.21 (d, J = 2.9 Hz, 1H), 7.18 (d, J = 2.9 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) δ 162.82,
156.46, 156.07, 151.30, 148.82, 145.99, 144.50, 139.93, 135.07, 134.31,
129.51, 129.13, 128.06, 127.46, 126.46, 124.28, 98.23.
156.46, 156.07, 151.30, 148.82, 145.99, 144.50, 139.93, 135.07, 134.31,
129.51, 129.13, 128.06, 127.46, 126.46, 124.28, 98.23.
[0026] 化合物7：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.80 – 7.65 (m, 2H), 7.52 – 7.42 (m, 2H), 7.15 (s, 1H), 3.96 (s, 3H).; 13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 148.17, 145.11, 136.77, 135.35, 134.15, 128.66, 128.58, 85.62, 37.40.
[0027] 化合物8：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.98 (d, J = 15.0 Hz, 1H), 7.96 (s, 1H), 7.70 (d, J = 3.1 Hz, 1H), 7.51 (dd, J = 15.0, 2.9 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 156.07, 148.17,
145.11, 136.77, 134.71, 134.56, 129.99, 129.74, 129.58, 128.24, 85.62,
37.40..
145.11, 136.77, 134.71, 134.56, 129.99, 129.74, 129.58, 128.24, 85.62,
37.40..
[0028] 化合物9：1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.37 (s, 1H), 8.19 (s, 1H), 8.10 – 8.03 (m, 2H), 7.86 (d, J = 15.0 Hz, 1H),
7.81 – 7.72 (m, 1H), 7.45 (dt, J = 15.0, 3.2 Hz, 1H), 7.31 (t, J = 14.9 Hz,
13
1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H). C NMR (125 MHz, DMSO-d6) δ 162.82,
156.46, 156.07, 151.30, 148.82, 145.99, 144.50, 139.93, 135.79, 132.84,
130.24, 128.06, 127.88, 124.76, 124.40, 124.28, 123.30, 98.23.
7.81 – 7.72 (m, 1H), 7.45 (dt, J = 15.0, 3.2 Hz, 1H), 7.31 (t, J = 14.9 Hz,
13
1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H). C NMR (125 MHz, DMSO-d6) δ 162.82,
156.46, 156.07, 151.30, 148.82, 145.99, 144.50, 139.93, 135.79, 132.84,
130.24, 128.06, 127.88, 124.76, 124.40, 124.28, 123.30, 98.23.
[0029] 化合物10：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 13
7.97 – 7.82 (m, 2H), 7.55 – 7.40 (m, 2H), 7.15 (s, 1H), 3.96 (s, 3H). C NMR (125 MHz, DMSO-d6) δ 161.05, 156.07, 148.17, 145.11, 137.42, 136.77, 132.35,
132.10, 131.97 (q, J = 31.5 Hz), 131.84), 131.59 , 127.21 (d, J = 1.5 Hz),
126.84, 125.96 (q, J = 3.7 Hz), 124.69 , 122.55, 120.40, 85.62, 37.40.
7.97 – 7.82 (m, 2H), 7.55 – 7.40 (m, 2H), 7.15 (s, 1H), 3.96 (s, 3H). C NMR (125 MHz, DMSO-d6) δ 161.05, 156.07, 148.17, 145.11, 137.42, 136.77, 132.35,
132.10, 131.97 (q, J = 31.5 Hz), 131.84), 131.59 , 127.21 (d, J = 1.5 Hz),
126.84, 125.96 (q, J = 3.7 Hz), 124.69 , 122.55, 120.40, 85.62, 37.40.
[0030] 化合物11：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.90 (d, J = 7.5 Hz, 2H), 7.15 (s, 1H), 7.11 (d, J = 7.5 Hz, 2H), 3.96 (s,
3H), 3.79 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ 161.04, 159.91, 156.07,
148.17, 145.11, 136.77, 128.59, 127.22, 114.03, 85.62, 56.08, 37.40.
3H), 3.79 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ 161.04, 159.91, 156.07,
148.17, 145.11, 136.77, 128.59, 127.22, 114.03, 85.62, 56.08, 37.40.
[0031] 化合物12：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.89 (d, J = 15.0 Hz, 2H), 7.15 (s, 1H), 7.05 (d, J = 15.0 Hz, 2H), 3.96 (s,
3H). 13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 150.43, 148.17, 145.11,
136.77, 130.16, 129.02, 121.36, 120.42, 85.62, 37.40.
3H). 13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 150.43, 148.17, 145.11,
136.77, 130.16, 129.02, 121.36, 120.42, 85.62, 37.40.
[0032] 化合物13：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 8.06 (t, J = 14.0 Hz, 1H), 3.96 (s, 3H), 2.37 (dt, J = 13.9, 10.8 Hz, 2H),
1.61 – 1.48 (m, 2H), 1.37 (ddd, J = 16.5, 10.1, 7.7 Hz, 2H), 0.93 (t, J =
12.9 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.53, 156.07, 148.17, 145.11,
136.77, 85.62, 37.40, 32.29, 30.45, 22.08, 14.00.
1.61 – 1.48 (m, 2H), 1.37 (ddd, J = 16.5, 10.1, 7.7 Hz, 2H), 0.93 (t, J =
12.9 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.53, 156.07, 148.17, 145.11,
136.77, 85.62, 37.40, 32.29, 30.45, 22.08, 14.00.
[0033] 化合物14：1H NMR (500 MHz, DMSO-d6 ) δ 8.37 (s, 1H), 8.19 (s, 1H), 8.15 (s, 1H), 7.80 (dt, J = 15.9, 2.9 Hz, 1H), 7.63 (td, J = 14.8, 9.8 Hz,
1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.44 (ddt, J = 15.9, 14.7, 3.2 Hz, 1H),
3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.47, 162.84, 162.81, 161.46,
156.07, 148.17, 145.11, 136.77, 136.57, 136.50, 130.29, 130.23, 125.07,
125.05, 115.87, 115.71, 114.91, 114.75, 85.62, 37.40.
1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.44 (ddt, J = 15.9, 14.7, 3.2 Hz, 1H),
3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.47, 162.84, 162.81, 161.46,
156.07, 148.17, 145.11, 136.77, 136.57, 136.50, 130.29, 130.23, 125.07,
125.05, 115.87, 115.71, 114.91, 114.75, 85.62, 37.40.
[0034] 化合物15：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.80 (dd, J = 10.1, 2.5 Hz, 1H), 7.79 – 7.76 (m, 1H), 7.32 – 7.24 (m, 2H),
13
7.15 (s, 1H); C NMR (125 MHz, DMSO-d6) δ 161.04, 160.08, 156.07, 148.17,
145.11, 136.77, 130.61, 130.51, 115.84, 85.62, 37.40.
13
7.15 (s, 1H); C NMR (125 MHz, DMSO-d6) δ 161.04, 160.08, 156.07, 148.17,
145.11, 136.77, 130.61, 130.51, 115.84, 85.62, 37.40.
[0035] 化合物16：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.96 (s, 1H), 7.27 – 7.13 (m, 1H), 7.11 (td, J = 15.4, 9.8 Hz, 1H), 3.96 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 165.42, 156.07, 148.17, 146.84, 146.51,
145.11, 141.88, 136.77, 126.53, 123.41, 115.16, 85.62, 37.40.
3H); 13C NMR (125 MHz, DMSO-d6) δ 165.42, 156.07, 148.17, 146.84, 146.51,
145.11, 141.88, 136.77, 126.53, 123.41, 115.16, 85.62, 37.40.
[0036] 化合物17：1H NMR (500 MHz, DMSO-d6 ) δ 8.18 (s, 1H), 8.14 (s, 1H), 8.04 (dd, J = 14.7, 3.2 Hz, 1H), 7.96 (s, 1H), 7.95 (dd, J = 14.2, 3.7 Hz,
2H), 7.69 (td, J = 14.9, 3.3 Hz, 1H), 7.58 (td, J = 14.8, 3.3 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 156.36, 156.07, 148.17, 146.90, 145.11,
136.77, 133.54, 131.67, 127.80, 127.11, 126.44, 85.62, 37.40.
2H), 7.69 (td, J = 14.9, 3.3 Hz, 1H), 7.58 (td, J = 14.8, 3.3 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 156.36, 156.07, 148.17, 146.90, 145.11,
136.77, 133.54, 131.67, 127.80, 127.11, 126.44, 85.62, 37.40.
[0037] 化合物18：1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.45 (t, J = 3.0 Hz, 1H), 8.37 (s, 1H), 8.19 (s, 1H), 8.11 (tt, J =
15.3, 3.0 Hz, 2H), 8.05 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.72 (t, J = 15.0
13
Hz, 1H), 7.20 (dd, J = 14.9, 3.0 Hz, 1H); C NMR (125 MHz, DMSO-d6) δ 162.82,
156.46, 156.07, 151.30, 148.82, 146.85, 145.99, 144.50, 139.93, 135.83,
132.97, 129.10, 128.06, 124.66, 124.28, 123.88, 98.23.
15.3, 3.0 Hz, 2H), 8.05 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.72 (t, J = 15.0
13
Hz, 1H), 7.20 (dd, J = 14.9, 3.0 Hz, 1H); C NMR (125 MHz, DMSO-d6) δ 162.82,
156.46, 156.07, 151.30, 148.82, 146.85, 145.99, 144.50, 139.93, 135.83,
132.97, 129.10, 128.06, 124.66, 124.28, 123.88, 98.23.
[0038] 化合物19：1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 3.1 Hz, 1H), 8.32 – 8.16 (m, 5H), 8.05 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J = 14.9, 3.0 Hz, 1H), 7.15 (s, 1H); 13C NMR (125 MHz, DMSO-d6) δ 161.04,
156.46, 156.07, 151.30, 148.82, 146.84, 145.99, 144.50, 139.93, 138.94,
128.06, 127.86, 124.28, 123.71, 98.23.
156.46, 156.07, 151.30, 148.82, 146.84, 145.99, 144.50, 139.93, 138.94,
128.06, 127.86, 124.28, 123.71, 98.23.
[0039] 化合物20：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H), 7.96 (s, 1H), 7.44 (dt, J = 15.0, 10.0 Hz, 1H), 7.13 (ddd, J = 16.0, 15.2,
3.1 Hz, 1H), 6.83 (td, J = 16.0, 3.0 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.68, 159.13, 156.07, 148.17, 145.11, 136.77, 130.39,
120.68, 113.03, 104.38, 85.62, 37.40.
3.1 Hz, 1H), 6.83 (td, J = 16.0, 3.0 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.68, 159.13, 156.07, 148.17, 145.11, 136.77, 130.39,
120.68, 113.03, 104.38, 85.62, 37.40.
[0040] 化合物21：1H NMR (500 MHz, DMSO-d6 ) δ 8.10 (s, 1H), 8.06 (s, 1H), 7.88 (s, 1H), 7.67 (ddd, J = 14.3, 2.1, 1.3 Hz, 1H), 7.55 – 7.49 (m, 2H),
7.49 – 7.37 (m, 1H); 13C NMR (125 MHz, DMSO-d6) δ 200.96, 160.12, 156.07,
148.17, 145.11, 136.77, 135.98, 129.24, 128.68, 127.92, 126.67, 125.29,
85.62, 37.40, 28.30.
7.49 – 7.37 (m, 1H); 13C NMR (125 MHz, DMSO-d6) δ 200.96, 160.12, 156.07,
148.17, 145.11, 136.77, 135.98, 129.24, 128.68, 127.92, 126.67, 125.29,
85.62, 37.40, 28.30.
[0041] 化合物22: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 8.05 (s, 1H), 7.96 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H),
7.74 – 7.66 (m, 1H), 7.26 – 7.16 (m, 4H), 2.43 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ 159.77, 156.46, 156.07, 151.30, 148.82, 145.99, 144.50, 139.93,
138.12, 132.93, 130.30, 128.63, 128.06, 126.98, 125.86, 124.28, 98.23, 20.07.[0042] 化合物23: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),
8.08 (q, J = 13.6 Hz, 1H), 3.96 (s, 3H), 2.18 (d, J = 13.6 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 162.39, 156.07, 148.17, 145.11, 136.77, 85.62, 37.40.[0043] 化合物24: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),
8.08 (q, J = 13.6 Hz, 1H), 3.96 (s, 3H), 2.18 (d, J = 13.6 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 162.39, 156.07, 148.17, 145.11, 136.77, 85.62, 37.40,[0044] 化合物25: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),
8.00 – 7.83 (m, 2H), 7.50 – 7.35 (m, 2H), 7.15 (s, 1H), 3.96 (s, 3H), 2.41 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 148.17, 145.11, 137.94,
136.77, 131.71, 128.60, 128.00, 85.62, 37.40, 21.15.
7.74 – 7.66 (m, 1H), 7.26 – 7.16 (m, 4H), 2.43 (s, 3H). 13C NMR (125 MHz, DMSO-d6) δ 159.77, 156.46, 156.07, 151.30, 148.82, 145.99, 144.50, 139.93,
138.12, 132.93, 130.30, 128.63, 128.06, 126.98, 125.86, 124.28, 98.23, 20.07.[0042] 化合物23: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),
8.08 (q, J = 13.6 Hz, 1H), 3.96 (s, 3H), 2.18 (d, J = 13.6 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 162.39, 156.07, 148.17, 145.11, 136.77, 85.62, 37.40.[0043] 化合物24: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),
8.08 (q, J = 13.6 Hz, 1H), 3.96 (s, 3H), 2.18 (d, J = 13.6 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 162.39, 156.07, 148.17, 145.11, 136.77, 85.62, 37.40,[0044] 化合物25: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),
8.00 – 7.83 (m, 2H), 7.50 – 7.35 (m, 2H), 7.15 (s, 1H), 3.96 (s, 3H), 2.41 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 148.17, 145.11, 137.94,
136.77, 131.71, 128.60, 128.00, 85.62, 37.40, 21.15.
[0045] 化合物26: 1H NMR (500 MHz, DMSO-d6 ) δ 9.27 (s, 1H), 8.19 (s, 1H), 7.96 (s, 1H), 7.51 (dd, J = 14.6, 3.0 Hz, 1H), 7.32 (td, J = 15.0, 3.0 Hz,
13
1H), 7.00 – 6.85 (m, 2H), 4.07 (s, 3H), 1.98 (s, 3H); C NMR (125 MHz, DMSO-d6) δ 163.25, 160.75, 159.91, 149.86, 147.07, 144.43, 131.03, 129.68, 121.02,
119.62, 116.26, 102.60, 38.34, 14.76.
13
1H), 7.00 – 6.85 (m, 2H), 4.07 (s, 3H), 1.98 (s, 3H); C NMR (125 MHz, DMSO-d6) δ 163.25, 160.75, 159.91, 149.86, 147.07, 144.43, 131.03, 129.68, 121.02,
119.62, 116.26, 102.60, 38.34, 14.76.
[0046] 化合物27: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.37 (s, 1H), 8.19 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.32 (dt, J =
15.0, 3.1 Hz, 1H), 7.25 (t, J = 3.0 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H),
7.14 (t, J = 14.9 Hz, 1H), 6.92 (dt, J = 15.0, 3.1 Hz, 1H), 4.75 (s, 1H),
1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 157.37, 154.71,
153.62, 148.96, 147.70, 143.15, 139.18, 136.93, 130.40, 127.96, 125.46,
120.90, 117.21, 115.08, 101.11, 14.76.
15.0, 3.1 Hz, 1H), 7.25 (t, J = 3.0 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H),
7.14 (t, J = 14.9 Hz, 1H), 6.92 (dt, J = 15.0, 3.1 Hz, 1H), 4.75 (s, 1H),
1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 157.37, 154.71,
153.62, 148.96, 147.70, 143.15, 139.18, 136.93, 130.40, 127.96, 125.46,
120.90, 117.21, 115.08, 101.11, 14.76.
[0047] 化合物28: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.08 (t, J = 14.0 Hz, 1H), 4.07 (s, 3H), 2.19 (p, J = 13.3 Hz, 2H), 1.98 (s, 3H), 1.01 (t, J = 13.2 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 166.60, 163.25, 149.86, 147.07,
144.43, 102.60, 38.34, 24.89, 14.76, 9.50.
144.43, 102.60, 38.34, 24.89, 14.76, 9.50.
[0048] 化合物29: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.96 (s, 1H), 7.52 (d, J = 2.1 Hz, 1H), 7.42 (ddd, J = 15.1, 2.2, 1.0 Hz, 1H), 7.28 (ddd, J = 15.0, 9.4, 8.3 Hz, 1H), 4.07 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.25, 149.86, 147.07, 144.43, 133.23, 130.43, 129.52, 129.18,
129.07, 127.60, 102.60, 38.34, 14.76.
129.07, 127.60, 102.60, 38.34, 14.76.
[0049] 化合物30:1H NMR (500 MHz, DMSO-d6 ) δ 8.37 (s, 1H), 8.19 (s, 1H), 7.73 (t, J = 2.9 Hz, 1H), 7.68 – 7.62 (m, 1H), 7.59 – 7.43 (m, 2H), 4.07 (s,
3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 223.26, 163.25, 162.82,
149.85, 147.08, 144.44, 135.08, 134.31, 129.51, 129.13, 127.46, 126.46,
102.60, 77.27, 38.33, 14.77, -19.95.
3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 223.26, 163.25, 162.82,
149.85, 147.08, 144.44, 135.08, 134.31, 129.51, 129.13, 127.46, 126.46,
102.60, 77.27, 38.33, 14.77, -19.95.
[0050] 化合物31: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.07 (t, J = 14.0 Hz, 1H), 4.07 (s, 3H), 2.31 (dd, J = 29.7, 15.6 Hz, 2H), 1.98 (s, 3H),
1.63 – 1.48 (m, 2H), 1.48 – 1.28 (m, 2H), 0.93 (t, J = 13.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.52, 163.25, 149.85, 147.08, 144.44, 102.60, 38.33,
32.29, 30.45, 22.08, 14.77, 14.00.
1.63 – 1.48 (m, 2H), 1.48 – 1.28 (m, 2H), 0.93 (t, J = 13.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.52, 163.25, 149.85, 147.08, 144.44, 102.60, 38.33,
32.29, 30.45, 22.08, 14.77, 14.00.
[0051] 化合物32: 1H NMR (500 MHz, DMSO-d6 ) δ 8.37 (s, 1H), 8.19 (s, 1H), 7.80 (dt, J = 16.0, 2.9 Hz, 1H), 7.62 (dd, J = 14.7, 9.8 Hz, 1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.45 (dt, J = 15.8, 8.9 Hz, 1H), 4.07 (s, 3H), 1.98 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 162.46, 149.86, 147.07,
144.43, 136.54, 130.26, 125.06, 115.79, 114.83, 102.60, 38.34, 14.76.
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 162.46, 149.86, 147.07,
144.43, 136.54, 130.26, 125.06, 115.79, 114.83, 102.60, 38.34, 14.76.
[0052] 化合物33: 1H NMR (500 MHz, DMSO-d6 ) δ 8.37 (s, 1H), 8.19 (s, 1H), 8.05 (t, J = 3.0 Hz, 1H), 7.76 (dt, J = 14.8, 3.1 Hz, 1H), 7.45 (dt, J =
15.0, 3.2 Hz, 1H), 7.31 (t, J = 14.9 Hz, 1H), 4.07 (s, 3H), 1.98 (s, 3H).; 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 149.85, 147.08, 144.44, 135.80,
135.79, 133.22, 132.96, 132.71, 132.45, 130.24, 127.91, 127.89, 127.87,
126.51, 124.80, 124.78, 124.75, 124.71, 124.45, 124.42, 124.37, 122.23,
120.08, 102.60, 38.33, 14.77.
15.0, 3.2 Hz, 1H), 7.31 (t, J = 14.9 Hz, 1H), 4.07 (s, 3H), 1.98 (s, 3H).; 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 149.85, 147.08, 144.44, 135.80,
135.79, 133.22, 132.96, 132.71, 132.45, 130.24, 127.91, 127.89, 127.87,
126.51, 124.80, 124.78, 124.75, 124.71, 124.45, 124.42, 124.37, 122.23,
120.08, 102.60, 38.33, 14.77.
[0053] 化合物34: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.94 – 7.82 (m, 2H), 7.55 – 7.35 (m, 2H), 7.15 (s, 1H), 4.07 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.05, 149.85, 147.08, 144.44, 137.42, 132.35,
132.10, 131.84, 131.59, 127.22, 127.20, 126.84, 126.00, 125.97, 125.94,
125.91, 124.69, 122.55, 120.40, 102.63, 38.31, 14.73.
132.10, 131.84, 131.59, 127.22, 127.20, 126.84, 126.00, 125.97, 125.94,
125.91, 124.69, 122.55, 120.40, 102.63, 38.31, 14.73.
[0054] 化合物35: 1H NMR (500 MHz, DMSO-d6 ) δ8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.92 – 7.89 (m, 1H), 7.87 (t, J = 2.4 Hz, 1H), 7.84 (t, J =
15.0 Hz, 1H), 7.20 (dd, J = 15.0, 3.1 Hz, 1H), 7.15 (s, 1H), 7.07 – 7.03 (m,
2H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 154.71,
153.62, 150.43, 148.96, 147.70, 143.15, 139.18, 130.16, 129.02, 127.96,
125.46, 121.36, 120.42, 101.11, 14.76.
15.0 Hz, 1H), 7.20 (dd, J = 15.0, 3.1 Hz, 1H), 7.15 (s, 1H), 7.07 – 7.03 (m,
2H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 154.71,
153.62, 150.43, 148.96, 147.70, 143.15, 139.18, 130.16, 129.02, 127.96,
125.46, 121.36, 120.42, 101.11, 14.76.
[0055] 化合物36: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.07 (t, J = 13.9 Hz, 1H), 4.07 (s, 3H), 2.35 (dt, J = 13.9, 11.4 Hz, 2H), 1.98 (s, 3H), 1.79 – 1.53 (m, 2H), 0.94 (t, J = 13.2 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.04,
163.25, 149.86, 147.07, 144.43, 102.60, 38.34, 32.25, 20.76, 14.76, 12.96.[0056] 化合物37: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.96 (s, 1H),
7.55 – 7.43 (m, 1H), 7.40 – 7.30 (m, 2H), 7.28 – 7.10 (m, 1H), 4.07 (s, 3H),
1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.25, 160.33, 149.86,
147.07, 144.43, 129.70, 128.39, 125.29, 123.83, 115.61, 102.60, 38.34, 14.76.[0057] 化合物38: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz,
1H), 8.37 (s, 1H), 8.19 (s, 1H), 7.81 (ddd, J = 15.9, 15.0, 8.9 Hz, 2H), 7.63 (td, J = 14.8, 9.8 Hz, 1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.48 – 7.39 (m,
1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 162.46, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18,
136.54, 130.26, 127.96, 125.46, 125.06, 115.79, 114.83, 101.11, 14.76.
163.25, 149.86, 147.07, 144.43, 102.60, 38.34, 32.25, 20.76, 14.76, 12.96.[0056] 化合物37: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.96 (s, 1H),
7.55 – 7.43 (m, 1H), 7.40 – 7.30 (m, 2H), 7.28 – 7.10 (m, 1H), 4.07 (s, 3H),
1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.25, 160.33, 149.86,
147.07, 144.43, 129.70, 128.39, 125.29, 123.83, 115.61, 102.60, 38.34, 14.76.[0057] 化合物38: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz,
1H), 8.37 (s, 1H), 8.19 (s, 1H), 7.81 (ddd, J = 15.9, 15.0, 8.9 Hz, 2H), 7.63 (td, J = 14.8, 9.8 Hz, 1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.48 – 7.39 (m,
1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 162.46, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18,
136.54, 130.26, 127.96, 125.46, 125.06, 115.79, 114.83, 101.11, 14.76.
[0058] 化合物39: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.81 – 7.76 (m, 2H), 7.28 (t, J = 7.8 Hz, 2H), 7.15 (s, 1H), 4.07 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 160.08, 149.86, 147.07, 144.43,
130.61, 130.51, 115.84, 102.60, 38.34, 14.76.
130.61, 130.51, 115.84, 102.60, 38.34, 14.76.
[0059] 化合物40: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.96 (s, 1H), 7.28 – 7.20 (m, 1H), 7.11 (td, J = 7.8, 5.0 Hz, 1H), 4.07 (s, 3H), 1.91 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 165.42, 163.25, 149.86, 147.07, 146.84,
146.51, 144.43, 141.88, 126.53, 123.41, 115.16, 102.60, 38.34, 14.76.
3H); 13C NMR (125 MHz, DMSO-d6) δ 165.42, 163.25, 149.86, 147.07, 146.84,
146.51, 144.43, 141.88, 126.53, 123.41, 115.16, 102.60, 38.34, 14.76.
[0060] 化合物41: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.04 (dd, J = 14.7, 3.2 Hz, 1H), 7.95 (dd, J = 14.2, 3.7 Hz, 2H), 7.69 (td, J = 14.9, 3.4 Hz, 1H), 7.59 (td, J = 14.9, 3.3 Hz, 1H), 4.17 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 156.36, 149.86, 147.07, 146.90, 144.43, 133.54,
131.67, 127.80, 127.11, 126.44, 102.60, 38.34, 14.76.
131.67, 127.80, 127.11, 126.44, 102.60, 38.34, 14.76.
[0061] 化合物42: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (t, J = 14.0 Hz, 1H), 4.07 (s, 3H), 3.80 (t, J = 15.3 Hz, 2H), 2.60 (td, J = 15.3,
14.1 Hz, 2H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 157.83,
149.86, 147.07, 144.43, 102.60, 39.44, 38.34, 31.28, 14.76.
14.1 Hz, 2H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 157.83,
149.86, 147.07, 144.43, 102.60, 39.44, 38.34, 31.28, 14.76.
[0062] 化合物43: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 14.9, 3.0 Hz, 1H), 8.31 – 8.17 (m, 5H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J = 15.0, 3.1 Hz, 1H), 7.15 (s, 1H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25,
161.04, 154.71, 153.62, 148.96, 147.70, 146.84, 143.15, 139.18, 138.94,
127.96, 127.86, 125.46, 123.71, 101.11, 14.76.
161.04, 154.71, 153.62, 148.96, 147.70, 146.84, 143.15, 139.18, 138.94,
127.96, 127.86, 125.46, 123.71, 101.11, 14.76.
[0063] 化合物44: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.96 (s, 1H), 7.44 (dt, J = 15.0, 10.0 Hz, 1H), 7.21 – 7.08 (m, 1H), 6.83 (td, J = 16.0,
3.0 Hz, 1H), 4.07 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69,
163.68, 163.25, 159.13, 149.86, 147.07, 144.43, 130.39, 120.68, 113.03,
104.38, 102.60, 38.34, 14.76.
3.0 Hz, 1H), 4.07 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69,
163.68, 163.25, 159.13, 149.86, 147.07, 144.43, 130.39, 120.68, 113.03,
104.38, 102.60, 38.34, 14.76.
[0064] 化合物45:1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.96 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.75 (ddd, J =
14.5, 2.2, 1.2 Hz, 1H), 7.62 – 7.46 (m, 3H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H),
2.62 (s, 3H), 1.94 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 200.96, 163.25,
160.12, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 135.98, 129.24,
128.68, 127.96, 127.92, 126.67, 125.46, 125.29, 101.11, 28.30.
14.5, 2.2, 1.2 Hz, 1H), 7.62 – 7.46 (m, 3H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H),
2.62 (s, 3H), 1.94 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 200.96, 163.25,
160.12, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 135.98, 129.24,
128.68, 127.96, 127.92, 126.67, 125.46, 125.29, 101.11, 28.30.
[0065] 化合物46: 1H NMR (500 MHz, DMSO-d6 ) δ 8.37 (s, 1H), 8.19 (s, 1H), 7.74 (t, J = 2.9 Hz, 1H), 7.73 – 7.60 (m, 1H), 7.33 (t, J = 14.9 Hz, 1H),
7.14 (dt, J = 14.8, 2.9 Hz, 1H), 4.07 (s, 3H), 2.42 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 149.86, 147.07, 144.43, 137.93,
135.44, 129.62, 129.55, 128.81, 124.22, 102.60, 38.34, 21.23, 14.76.
7.14 (dt, J = 14.8, 2.9 Hz, 1H), 4.07 (s, 3H), 2.42 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 149.86, 147.07, 144.43, 137.93,
135.44, 129.62, 129.55, 128.81, 124.22, 102.60, 38.34, 21.23, 14.76.
[0066] 化合物47: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.96 (s, 1H), 7.71 (dq, J = 5.7, 2.7 Hz, 1H), 7.32 – 7.11 (m, 3H), 4.07 (s, 3H), 2.43 (s,
3H), 1.87 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 159.77, 149.86,
147.07, 144.43, 138.12, 132.93, 130.30, 128.63, 126.98, 125.86, 102.60,
38.34, 20.07, 14.76.
3H), 1.87 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 159.77, 149.86,
147.07, 144.43, 138.12, 132.93, 130.30, 128.63, 126.98, 125.86, 102.60,
38.34, 20.07, 14.76.
[0067] 化合物48: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 7.95 – 7.87 (m, 2H), 7.47 – 7.35 (m, 2H), 7.15 (s, 1H), 4.07 (s, 3H), 2.41 (s, 3H), 1.92(s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 149.86, 147.07, 144.43,
137.94, 131.71, 128.60, 128.00, 102.60, 38.34, 21.15, 14.76.
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 149.86, 147.07, 144.43,
137.94, 131.71, 128.60, 128.00, 102.60, 38.34, 21.15, 14.76.
[0068] 化合物49：1H NMR (500 MHz, DMSO-d6) δ 9.26 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 9.01 (s, 1H, pyridine-H), 8.75 (d, J = 4.5 Hz, 1H, pyridine-H), 8.59 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.30 (d, J = 7.9 Hz, 1H, pyridine-H), 8.16 (s, 1H, -CH=N), 7.61 – 7.53 (m, 1H, pyridine-H), 3.92 (s,
13
3H, -NCH3); C NMR (125 MHz, DMSO-d6) δ 164.36, 154.55, 153.53, 150.69,
150.49, 148.64, 135.56, 135.45, 129.02, 124.82, 105.97, 34.68. IR (KBr):ν
3444.8, 3041.7, 1693.5, 1593.2, 1568.1, 1541.1, 1145.7 cm-1
13
3H, -NCH3); C NMR (125 MHz, DMSO-d6) δ 164.36, 154.55, 153.53, 150.69,
150.49, 148.64, 135.56, 135.45, 129.02, 124.82, 105.97, 34.68. IR (KBr):ν
3444.8, 3041.7, 1693.5, 1593.2, 1568.1, 1541.1, 1145.7 cm-1
[0069] 化合物50：1H NMR (500 MHz, DMSO-d6) δ 9.37 (s, 1H, thiazole-H), 9.26 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.52 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.14 (s, 1H, -CH=N), 3.91 (s, 3H, -NCH3), 2.55 (s, 3H, -CH3); 13C NMR (125 MHz, DMSO-d6) δ 160.43, 159.99, 158.75, 154.41, 150.55, 148.24, 135.36, 126.18, 105.92, 34.63, 16.18. IR (KBr):ν3444.8, 3041.7, 1693.5, 1593.2, -1
1568.1, 1541.1, 1145.7 cm .
1568.1, 1541.1, 1145.7 cm .
[0070] 化合物51：1H NMR (500 MHz, DMSO-d6) δ 8.97 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.49 (s, 1H, pyrazolo[3,4-d]pyrimidin), 8.13 (s, 1H, -CH=N), 8.03 (d, 4J = 1.5 Hz, 1H, furan-H), 7.27 (d, 1H, 3J = 3.5 Hz, furan-H), 6.75 (dd, 3J = 3.5, 4J =1.8 Hz, 1H, furan-H), 3.91 (s, 3H, -NCH3), 3.31 (s, 3H, -CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.35, 154.61, 150.48, 148.65, 148.34,
148.04, 135.34, 120.56, 113.45, 105.98,34.62. IR (KBr):ν3444.8, 3147.8,
1701.2, 1616.3, 1575.8, 1473.6, 927.6 cm-1.
148.04, 135.34, 120.56, 113.45, 105.98,34.62. IR (KBr):ν3444.8, 3147.8,
1701.2, 1616.3, 1575.8, 1473.6, 927.6 cm-1.
[0071] 化合物52：1H NMR (500 MHz, DMSO-d6) δ 8.81 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.46 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.11 (s, 1H, -CH=N), 3.91 (s, 3H, -NCH3), 3.78 (s, 3H, -NCH3), 2.37 (s, 3H, -CH3). 13C NMR (125 MHz, DMSO-d6) δ 160.37, 154.52, 150.64, 148.73, 148.44, 135.22, 130.93, 110.35, 106.09, 36.73, 34.60, 14.80.
[0072] 化合物53: 1H NMR (500 MHz, DMSO-d6 ) δ 8.40 – 8.34 (m, 2H), 8.19 (s, 1H), 7.96 (s, 1H), 7.94 – 7.77 (m, 3H), 7.72 – 7.66 (m, 1H), 7.48 – 7.41 (m,
1H), 7.37 – 7.23 (m, 2H), 1.89 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.36,
163.25, 152.70, 150.90, 143.15, 140.81, 130.52, 128.97, 128.97, 128.55,
128.19, 126.96, 126.74, 125.67, 125.03, 123.87, 104.75, 14.76.
1H), 7.37 – 7.23 (m, 2H), 1.89 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.36,
163.25, 152.70, 150.90, 143.15, 140.81, 130.52, 128.97, 128.97, 128.55,
128.19, 126.96, 126.74, 125.67, 125.03, 123.87, 104.75, 14.76.
[0073] 化合物54: 1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.37 (dd, J = 3.3, 1.5 Hz, 1H), 8.19 (s, 1H), 7.94 – 7.76 (m, 5H), 7.49 – 7.44 (m, 1H), 7.45 – 7.41 (m, 1H), 7.15 (s, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 152.70, 150.90, 143.15, 140.81, 137.42,
131.97, 128.97, 128.97, 127.21, 125.96, 125.03, 123.62, 104.75, 14.76.
131.97, 128.97, 128.97, 127.21, 125.96, 125.03, 123.62, 104.75, 14.76.
[0074] 化合物55: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 3.1 Hz, 1H), 8.19 (s, 1H), 8.10 (t, J = 14.0 Hz, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H), 2.30 (dd, J = 29.8, 15.6 Hz, 2H), 1.98 (s, 3H),
1.53 (ddd, J = 30.2, 15.1, 1.9 Hz, 2H), 1.42 – 1.28 (m, 2H), 0.93 (t, J =
12.9 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.53, 163.25, 154.71, 153.62,
148.96, 147.70, 143.15, 139.18, 127.96, 125.46, 101.11, 32.29, 30.45, 22.08,
14.76, 14.00.
1.53 (ddd, J = 30.2, 15.1, 1.9 Hz, 2H), 1.42 – 1.28 (m, 2H), 0.93 (t, J =
12.9 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.53, 163.25, 154.71, 153.62,
148.96, 147.70, 143.15, 139.18, 127.96, 125.46, 101.11, 32.29, 30.45, 22.08,
14.76, 14.00.
[0075] 化合物56: 1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.37 (dd, J = 3.2, 1.5 Hz, 1H), 8.19 (s, 1H), 7.96 – 7.76 (m, 5H), 7.15 (s, 1H), 7.08 – 7.02 (m, 2H), 1.97 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
163.25, 161.04, 152.70, 150.90, 150.43, 143.15, 140.81, 130.16, 129.02,
128.97, 128.97, 125.03, 121.36, 120.42, 104.75, 14.76.
163.25, 161.04, 152.70, 150.90, 150.43, 143.15, 140.81, 130.16, 129.02,
128.97, 128.97, 125.03, 121.36, 120.42, 104.75, 14.76.
[0076] 化合物57: 1H NMR (500 MHz, DMSO-d6 ) δ 8.38 (dd, J = 7.5, 1.2 Hz, 2H), 8.19 (s, 1H), 7.96 (s, 1H), 7.89 (t, J = 7.4 Hz, 2H), 7.84 – 7.77 (m,
1H), 7.49 – 7.44 (m, 1H), 7.39 – 7.33 (m, 2H), 7.20 – 7.13 (m, 1H), 1.98 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.25, 160.33, 152.70, 150.90,
143.15, 140.81, 129.70, 128.97, 128.97, 128.39, 125.29, 125.03, 123.83,
115.61, 104.75, 14.76.
1H), 7.49 – 7.44 (m, 1H), 7.39 – 7.33 (m, 2H), 7.20 – 7.13 (m, 1H), 1.98 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.25, 160.33, 152.70, 150.90,
143.15, 140.81, 129.70, 128.97, 128.97, 128.39, 125.29, 125.03, 123.83,
115.61, 104.75, 14.76.
[0077] 化合物59: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.94 – 7.70 (m, 3H), 7.32 – 7.09 (m, 4H), 1.92 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04, 160.08, 154.71, 153.62, 148.96,
147.70, 143.15, 139.18, 130.61, 130.51, 127.96, 125.46, 115.84, 101.11,
14.76.
147.70, 143.15, 139.18, 130.61, 130.51, 127.96, 125.46, 115.84, 101.11,
14.76.
[0078] 化合物60: 1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.7, 2.3 Hz, 1H), 8.36 (dt, J = 6.5, 3.4 Hz, 1H), 8.19 (s, 1H), 7.96 (s, 1H), 7.93 – 7.76 (m, 3H), 7.16 (tdd, J = 30.8, 15.1, 9.8 Hz, 2H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 165.42, 163.25, 152.70, 150.90, 146.84, 146.51, 143.15,
141.88, 140.81, 128.97, 128.97, 126.53, 125.03, 123.41, 115.16, 104.75,
14.76.
141.88, 140.81, 128.97, 128.97, 126.53, 125.03, 123.41, 115.16, 104.75,
14.76.
[0079] 化合物61: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 8.10 (t, J = 13.9 Hz, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H), 2.38 – 2.20 (m, 2H), 1.98 (s, 3H), 1.81 – 1.53 (m, 2H), 0.94 (t, J = 13.2 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.04,
163.25, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 127.96, 125.46,
101.11, 32.25, 20.76, 14.76, 12.96.
163.25, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 127.96, 125.46,
101.11, 32.25, 20.76, 14.76, 12.96.
[0080] 化合物62:1H NMR (500 MHz, DMSO-d6 ) δ 8.45 (t, J = 3.0 Hz, 1H), 8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.37 (d, J = 3.8 Hz, 2H), 8.19 (s, 1H), 8.11 (tt, 13
J = 15.3, 3.0 Hz, 2H), 7.94 – 7.76 (m, 3H), 7.72 (t, J = 14.9 Hz, 1H); C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 152.70, 150.90, 146.85, 143.15, 140.81,
135.83, 132.97, 129.10, 128.97, 128.97, 125.03, 124.66, 123.88, 104.75,
14.76.
J = 15.3, 3.0 Hz, 2H), 7.94 – 7.76 (m, 3H), 7.72 (t, J = 14.9 Hz, 1H); C NMR (125 MHz, DMSO-d6) δ 163.25, 162.82, 152.70, 150.90, 146.85, 143.15, 140.81,
135.83, 132.97, 129.10, 128.97, 128.97, 125.03, 124.66, 123.88, 104.75,
14.76.
[0081] 化合物63: 1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.8, 2.4 Hz, 1H), 8.36 (dt, J = 6.5, 3.4 Hz, 1H), 8.30 – 8.18 (m, 5H), 7.94 – 7.77 (m,
3H), 7.15 (s, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04,
152.70, 150.90, 146.84, 143.15, 140.81, 138.94, 128.97, 128.97, 127.86,
125.03, 123.71, 104.75, 14.76.
3H), 7.15 (s, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04,
152.70, 150.90, 146.84, 143.15, 140.81, 138.94, 128.97, 128.97, 127.86,
125.03, 123.71, 104.75, 14.76.
[0082] 化合物64: 1H NMR (500 MHz, DMSO-d6 ) δ 8.43 – 8.32 (m, 1H), 8.19 (s, 1H), 8.00 – 7.75 (m, 2H), 7.44 (dt, J = 15.0, 10.0 Hz, 1H), 7.20 – 7.07 (m,
1H), 7.00 (td, J = 15.9, 2.9 Hz, 1H), 1.98 (s, 2H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.68, 163.25, 159.13, 152.70, 150.90, 143.15, 140.81, 130.39,
128.97, 128.97, 125.03, 120.68, 113.03, 104.75, 104.38, 14.76.
1H), 7.00 (td, J = 15.9, 2.9 Hz, 1H), 1.98 (s, 2H); 13C NMR (125 MHz, DMSO-d6) δ 165.69, 163.68, 163.25, 159.13, 152.70, 150.90, 143.15, 140.81, 130.39,
128.97, 128.97, 125.03, 120.68, 113.03, 104.75, 104.38, 14.76.
[0083] 化合物65: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.96 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.75 (ddd, J =
14.5, 2.2, 1.2 Hz, 1H), 7.63 – 7.45 (m, 3H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H),
2.62 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 200.96, 163.25,
160.12, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 135.98, 129.24,
128.68, 127.96, 127.92, 126.67, 125.46, 125.29, 101.11, 28.30, 14.76.
14.5, 2.2, 1.2 Hz, 1H), 7.63 – 7.45 (m, 3H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H),
2.62 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 200.96, 163.25,
160.12, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 135.98, 129.24,
128.68, 127.96, 127.92, 126.67, 125.46, 125.29, 101.11, 28.30, 14.76.
[0084] 化合物66: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.29 – 8.14 (m, 2H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H), 3.80 (t, J = 15.8 Hz, 2H), 2.58 (td, J = 15.7, 14.2 Hz, 2H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 157.83, 154.71, 153.62, 148.96,
147.70, 143.15, 139.18, 127.96, 125.46, 101.11, 39.44, 31.28, 14.76.
147.70, 143.15, 139.18, 127.96, 125.46, 101.11, 39.44, 31.28, 14.76.
[0085] 化合物67: 1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.96 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.78 – 7.65 (m,
1H), 7.33 – 7.15 (m, 4H), 2.43 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 159.77, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 138.12,
132.93, 130.30, 128.63, 127.96, 126.98, 125.86, 125.46, 101.11, 20.07, 14.76.[0086] 化合物68: 1H NMR (500 MHz, DMSO-d6 ) δ 8.41 – 8.34 (m, 2H), 8.19 (s,
1H), 7.94 – 7.88 (m, 3H), 7.87 – 7.76 (m, 2H), 7.44 – 7.36 (m, 2H), 7.15 (s,
1H), 2.41 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04,
152.70, 150.90, 143.15, 140.81, 137.94, 131.71, 128.97, 128.97, 128.60,
128.00, 125.03, 104.75, 21.15, 14.76.
1H), 7.33 – 7.15 (m, 4H), 2.43 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 159.77, 154.71, 153.62, 148.96, 147.70, 143.15, 139.18, 138.12,
132.93, 130.30, 128.63, 127.96, 126.98, 125.86, 125.46, 101.11, 20.07, 14.76.[0086] 化合物68: 1H NMR (500 MHz, DMSO-d6 ) δ 8.41 – 8.34 (m, 2H), 8.19 (s,
1H), 7.94 – 7.88 (m, 3H), 7.87 – 7.76 (m, 2H), 7.44 – 7.36 (m, 2H), 7.15 (s,
1H), 2.41 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 161.04,
152.70, 150.90, 143.15, 140.81, 137.94, 131.71, 128.97, 128.97, 128.60,
128.00, 125.03, 104.75, 21.15, 14.76.
[0087] 化合物69: 1H NMR (500 MHz, DMSO-d6 ) δ 8.28 (s, 1H), 8.19 (s, 2H), 8.15 (s, 1H), 6.95 (dd, J = 14.9, 3.0 Hz, 1H), 6.51 (dd, J = 15.0, 3.1 Hz,
1H), 6.15 (t, J = 14.9 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
156.07, 148.17, 147.53, 145.11, 136.77, 126.26, 122.79, 116.16, 110.32,
85.62, 37.40.
1H), 6.15 (t, J = 14.9 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
156.07, 148.17, 147.53, 145.11, 136.77, 126.26, 122.79, 116.16, 110.32,
85.62, 37.40.
[0088] 化合物70： 1H NMR (500 MHz, DMSO-d6) δ 9.33 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.77 (dd, 3J = 4.4 Hz, 4J = 1.5 Hz, 1H, pyridine-H), 8.74 (dd, 3J = 4.4 Hz, 4J = 1.5 Hz, 1H, pyridine-H), 8.60 (s, 1H, pyrazolo[3,4-d]
pyrimidine-H), 8.17 (s, 1H, -CH=N), 7.82 (dd, 3J = 4.5 Hz, 4J = 1.5 Hz, 1H, pyridine-H), 7.77 (dd, 3J = 4.3 Hz, 4J = 1.5 Hz, 1H, pyridine-H); 13C NMR (125 MHz, DMSO-d6) δ 163.63, 151.25, 151.17, 148.96, 140.19, 135.58, 123.28,
122.56, 105.97, 34.70.
pyrimidine-H), 8.17 (s, 1H, -CH=N), 7.82 (dd, 3J = 4.5 Hz, 4J = 1.5 Hz, 1H, pyridine-H), 7.77 (dd, 3J = 4.3 Hz, 4J = 1.5 Hz, 1H, pyridine-H); 13C NMR (125 MHz, DMSO-d6) δ 163.63, 151.25, 151.17, 148.96, 140.19, 135.58, 123.28,
122.56, 105.97, 34.70.
[0089] 化合物71：1H NMR (500 MHz, DMSO-d6) δ 9.25 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.73 (ddd, J = 4.8, 1.7, 1.0 Hz, 1H, pyridine-H), 8.60 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.17 (s, 1H, -CH=N), 8.13 (dt, J = 7.9, 1.0 Hz, 1H, pyridine-H), 7.98 (td, J = 7.7, 1.6 Hz, 1H, pyridine-H), 7.57 (ddd, J =
7.5, 4.8, 1.2 Hz, 1H, pyridine-H), 3.92 (s, 3H, -NCH3); 13C NMR (125 MHz, DMSO-d6) δ 165.32, 154.83, 151.96, 150.65, 149.03, 137.91, 135.59, 126.95,
122.20, 120.00, 106.06, 34.67. IR (KBr):ν 3444.8, 3105.3, 1707.0, 1570.1,
1539.2, 1255.6, 765.7 cm-1.
7.5, 4.8, 1.2 Hz, 1H, pyridine-H), 3.92 (s, 3H, -NCH3); 13C NMR (125 MHz, DMSO-d6) δ 165.32, 154.83, 151.96, 150.65, 149.03, 137.91, 135.59, 126.95,
122.20, 120.00, 106.06, 34.67. IR (KBr):ν 3444.8, 3105.3, 1707.0, 1570.1,
1539.2, 1255.6, 765.7 cm-1.
[0090] 化合物72：1H NMR (500 MHz, DMSO-d6) δ 9.04 (d, J = 1.8 Hz, 1H, pyridine-H), 8.94 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.77 (dd, J = 4.8,
1.7 Hz, 1H, pyridine-H), 8.34 (dt, J = 8.0, 1.9 Hz, 1H, pyridine-H), 8.08 (s,
1H, -CH=N), 7.59 (dd, J = 7.9, 4.8 Hz, 1H, pyridine-H), 3.88 (s, 3H, -NCH3),
2.51 (s, 3H, -CH3). 13C NMR (125 MHz, DMSO-d6) δ 167.91, 156.97, 154.26,
153.73, 150.71, 149.90, 135.77, 135.25, 128.84, 124.88, 104.42, 34.47, 23.13.[0091] 化合物73：1H NMR (500 MHz, Chloroform-D) δ 8.76 – 8.57 (m, 1H), 8.05 (d, J = 4.2 Hz, 1H), 7.68 (d, J = 7.4 Hz, 1H), 7.26 (d, J = 4.2 Hz, 1H), 7.05 (s, 1H), 6.60 (d, J = 6.8 Hz, 1H), 3.96 (s, 3H), 2.62 (s, 3H); 13C NMR (125 MHz, Chloroform-D) δ 157.06, 155.14, 148.01, 146.92, 135.44, 118.94, 112.64,
104.63, 34.18, 23.23.
1.7 Hz, 1H, pyridine-H), 8.34 (dt, J = 8.0, 1.9 Hz, 1H, pyridine-H), 8.08 (s,
1H, -CH=N), 7.59 (dd, J = 7.9, 4.8 Hz, 1H, pyridine-H), 3.88 (s, 3H, -NCH3),
2.51 (s, 3H, -CH3). 13C NMR (125 MHz, DMSO-d6) δ 167.91, 156.97, 154.26,
153.73, 150.71, 149.90, 135.77, 135.25, 128.84, 124.88, 104.42, 34.47, 23.13.[0091] 化合物73：1H NMR (500 MHz, Chloroform-D) δ 8.76 – 8.57 (m, 1H), 8.05 (d, J = 4.2 Hz, 1H), 7.68 (d, J = 7.4 Hz, 1H), 7.26 (d, J = 4.2 Hz, 1H), 7.05 (s, 1H), 6.60 (d, J = 6.8 Hz, 1H), 3.96 (s, 3H), 2.62 (s, 3H); 13C NMR (125 MHz, Chloroform-D) δ 157.06, 155.14, 148.01, 146.92, 135.44, 118.94, 112.64,
104.63, 34.18, 23.23.
[0092] 化合物74：1H NMR (500 MHz, Chloroform-D) δ 9.02 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.75 (d, J = 4.7 Hz, 1H, pyridine-H), 8.16 (d, J = 7.9 Hz, 1H, pyridine-H), 8.07 (s, 1H, -CH=N), 7.84 (td, J = 7.7, 1.5 Hz, 1H,
pyridine-H)), 7.46 – 7.40 (m, 1H, pyridine-H), 3.99 (s, 3H, -NCH3), 2.64 (s,
3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 167.02, 160.68, 157.07, 154.74,
152.02, 150.23, 136.79, 135.66, 126.03, 122.23, 104.69, 34.22, 23.28.
pyridine-H)), 7.46 – 7.40 (m, 1H, pyridine-H), 3.99 (s, 3H, -NCH3), 2.64 (s,
3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 167.02, 160.68, 157.07, 154.74,
152.02, 150.23, 136.79, 135.66, 126.03, 122.23, 104.69, 34.22, 23.28.
[0093] 化合物75： 1H NMR (500 MHz, Chloroform-D) δ9.02 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 7.98 (s, 1H), 7.82 (s, 1H), 3.85 (s, 3H), 3.02 (s, 3H), 2.99 13
(s, 3H), 2.52 (s, 3H)；C NMR (125 MHz, Chloroform-D) δ 162.96, 157.09,
148.42, 145.69, 104.28, 41.24, 34.77, 33.80, 13.56.
(s, 3H), 2.52 (s, 3H)；C NMR (125 MHz, Chloroform-D) δ 162.96, 157.09,
148.42, 145.69, 104.28, 41.24, 34.77, 33.80, 13.56.
[0094] 化合物77：1H NMR (500 MHz, DMSO-d6) δ 9.32 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.52 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.13 (s, 1H, -CH=N), 8.03 – 7.93 (m, 1H, benzene-H), 7.57 (dd, J = 13.5, 7.0 Hz, 1H, benzene-H), 7.24 – 7.15 (m, 1H, benzene-H), 7.07 (dd, J = 13.9, 7.0 Hz, 1H, benzene-H), 3.92 (s, 3H, -CH3), 3.86 (s, 3H, -CH3).
[0095] 化合物78：1H NMR (500 MHz, DMSO-d6 ) δ 8.94 – 8.82 (m, 1H), 8.81 – 8.65 (m, 1H), 8.36 (s, 1H), 8.19 (s, 1H), 8.06 (dt, J = 15.0, 3.0 Hz, 1H),
7.34 (t, J = 15.0 Hz, 1H), 4.07 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 150.92, 149.86, 149.58, 148.89, 147.07, 144.43, 137.24, 134.12,
124.05, 102.60, 38.34, 14.76
7.34 (t, J = 15.0 Hz, 1H), 4.07 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 150.92, 149.86, 149.58, 148.89, 147.07, 144.43, 137.24, 134.12,
124.05, 102.60, 38.34, 14.76
[0096] 化合物79：1H NMR (500 MHz, Chloroform-D) δ 7.98 (s, 1H), 7.82 (s, 1H), 3.85 (s, 3H), 3.02 (s, 3H), 2.99 (s, 3H), 2.52 (s, 3H)；13C NMR (125 MHz, Chloroform-D) δ 162.96, 157.09, 148.42, 145.69, 104.28, 41.24, 34.77, 33.80,
13.56.
13.56.
[0097] 化合物80：1H NMR (500 MHz, Chloroform-D) δ 7.65 (s, 1H), 3.86 (s, 3H), 2.54 (s, 3H), 2.50 (s, 3H)；13C NMR (125 MHz, Chloroform-D) δ 162.34, 157.73,
157.57, 150.54, 145.48, 102.85, 33.61, 23.27, 13.52.
157.57, 150.54, 145.48, 102.85, 33.61, 23.27, 13.52.
[0098] 化合物81：1H NMR (500 MHz, Chloroform-D) δ 8.87 (s, 1H,-CH=N), 7.95 – 7.81 (m, 2H, Ar-H), 7.50 (dt, J = 8.4, 7.2 Hz, 3H, Ar-H), 3.90 (s, 3H, -
NCH3), 2.60 (s, 3H, -CH3), 2.57 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 166.86, 146.33, 132.75, 132.55, 129.03, 128.91, 102.75, 77.37, 77.12,
76.86, 33.74, 23.26, 13.59;
NCH3), 2.60 (s, 3H, -CH3), 2.57 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 166.86, 146.33, 132.75, 132.55, 129.03, 128.91, 102.75, 77.37, 77.12,
76.86, 33.74, 23.26, 13.59;
[0099] 化合物82：1H NMR (500 MHz, Chloroform-D) δ 9.19 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.25 (s, 1H,-CH=N-), 6.86 (d, J = 3.4 Hz, 1H, furan-H), 6.20 (d, J = 3.3 Hz, 1H, furan-H), 3.92 (s, 3H, -NCH3), 2.58 (s, 3H, -CH3), 2.43 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 158.00, 156.65, 151.76, 150.55, 149.06, 146.59, 146.44, 121.47, 109.36, 104.28, 33.98, 14.20, 13.66.[0100] 化合物83：1H NMR (500 MHz, Chloroform-D) δ 8.47 (s, 1H, -CH=N-), 6.91 (d, J = 3.4 Hz, 1H, furan-H), 6.21 (d, J = 3.3 Hz, 1H, furan-H), 3.89 (s, 3H, -NCH3), 2.60 (s, 3H, -CH3), 2.56 (s, 3H, -CH3), 2.44 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 158.25, 156.98, 155.74, 155.26, 150.37, 146.28,
146.25, 121.56, 109.37, 102.61, 33.71, 23.23, 14.21, 13.56.
146.25, 121.56, 109.37, 102.61, 33.71, 23.23, 14.21, 13.56.
[0101] 化合物84：1H NMR (500 MHz, Chloroform-D) δ 9.78 (s, 1H), 9.45 (s, 1H), 8.21 (s, 1H), 7.83 (s, 1H), 7.57 (s, 1H), 3.93 (s, 3H), 2.60 (s, 3H)；13C NMR (125 MHz, Chloroform-D) δ 163.25, 149.86, 147.07, 146.08, 144.43, 143.76,
133.40, 125.39, 102.60, 38.34, 14.76.
133.40, 125.39, 102.60, 38.34, 14.76.
[0102] 化合物85：1H NMR (500 MHz, Chloroform-D) δ 9.78 (s, 1H), 8.21 (s, 1H), 7.83 (s, 1H), 7.57 (s, 1H), 3.90 (s, 3H, -NCH3), 2.58 (s, 3H, -CH3), 2.57 (s,
3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 164.05, 157.60, 150.14, 149.86,
146.93, 146.08, 133.40, 125.39, 107.61, 38.34, 20.90, 14.76.
3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 164.05, 157.60, 150.14, 149.86,
146.93, 146.08, 133.40, 125.39, 107.61, 38.34, 20.90, 14.76.
[0103] 化合物86：1H NMR (500 MHz, Chloroform-D) δ 8.84 (s, 1H, -CH=N-), 7.84 4 3
(d, J = 2.8 Hz, 1H, thiophene-H), 7.67 (d, J = 5.0 Hz, 1H, thiophene-H),
7.42 (dd, 3J = 5.0, 4J = 3.0 Hz, 1H, thiophene-H), 3.90 (s, 3H, -NCH3), 2.58 (s, 3H, -CH3), 2.57 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 161.49,
157.04, 155.85, 150.39, 148.45, 146.30, 136.20, 127.36, 125.25, 102.72,
33.74, 23.21, 13.57.
(d, J = 2.8 Hz, 1H, thiophene-H), 7.67 (d, J = 5.0 Hz, 1H, thiophene-H),
7.42 (dd, 3J = 5.0, 4J = 3.0 Hz, 1H, thiophene-H), 3.90 (s, 3H, -NCH3), 2.58 (s, 3H, -CH3), 2.57 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 161.49,
157.04, 155.85, 150.39, 148.45, 146.30, 136.20, 127.36, 125.25, 102.72,
33.74, 23.21, 13.57.
[0104] 化合物87：1H NMR (500 MHz, Chloroform-D) δ 9.49 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.21 (s, 1H, -CH=N-), 7.80 (d, 4J = 2.3 Hz, 1H, thiophene-H), 7.63 (d, 3J = 5.2 Hz, 1H, thiophene-H), 7.41 (dd, 3J = 5.1, 4J = 2.9 Hz, 1H, thiophene-H), 3.94 (s, 3H, -NCH3), 2.60 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 158.29, 156.69, 150.60, 149.11, 146.64, 136.57, 131.87,
127.35, 124.97, 104.35, 34.00, 13.68.
127.35, 124.97, 104.35, 34.00, 13.68.
[0105] 化合物88：1H NMR (500 MHz, Chloroform-D) δ 8.89 (s, 1H, -CH=N-), 7.31 (d, J = 3.6 Hz, 1H, thiophene-H), 6.81 (d, 1H, J = 3.3 Hz, thiophene-H), 3.89 (s, 3H, -NCH3), 2.57 (s, 3H, -CH3), 2.562 (s, 3H, -CH3), 2.558 (s, 3H, -CH3). 13
C NMR (125 MHz, Chloroform-D) δ 160.31, 157.21, 156.05, 150.33, 147.51,
146.25, 135.15, 126.60, 102.69, 33.71, 23.18, 16.11, 13.55.
C NMR (125 MHz, Chloroform-D) δ 160.31, 157.21, 156.05, 150.33, 147.51,
146.25, 135.15, 126.60, 102.69, 33.71, 23.18, 16.11, 13.55.
[0106] 化合物89：1H NMR (500 MHz, Chloroform-D) δ 9.52 (s, 1H, pyridine-H), 8.18 (s, 1H, -CH=N-), 7.29 (d, J = 3.6 Hz, 1H, pyridine-H), 6.80 (dd, J =
3.4, 0.8 Hz, 1H, pyridine-H), 3.92 (s, 3H, -NCH3), 2.59 (s, 3H, -CH3), 2.55 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 157.55, 156.79, 150.59,
149.06, 147.09, 146.55, 135.42, 134.90, 126.56, 104.29, 33.95, 16.07, 13.62.[0107] 化合物90：1H NMR (500 MHz, Chloroform-D) δ 9.12 (s, 1H, pyridine-H),
8.72 (d, J = 2.3 Hz, 1H, pyridine-H), 8.09 (dd, J = 8.3, 2.4 Hz, 1H,
pyridine-H), 7.62 (d, J = 8.4 Hz, 1H, pyridine-H), 3.90 (s, 3H, -NCH3), 2.66 (s, 3H, -CH3), 2.61 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 161.11,
159.75, 158.47, 157.28, 150.80, 146.57, 136.62, 128.77, 128.43, 108.51,
33.76, 23.32, 13.53.
3.4, 0.8 Hz, 1H, pyridine-H), 3.92 (s, 3H, -NCH3), 2.59 (s, 3H, -CH3), 2.55 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 157.55, 156.79, 150.59,
149.06, 147.09, 146.55, 135.42, 134.90, 126.56, 104.29, 33.95, 16.07, 13.62.[0107] 化合物90：1H NMR (500 MHz, Chloroform-D) δ 9.12 (s, 1H, pyridine-H),
8.72 (d, J = 2.3 Hz, 1H, pyridine-H), 8.09 (dd, J = 8.3, 2.4 Hz, 1H,
pyridine-H), 7.62 (d, J = 8.4 Hz, 1H, pyridine-H), 3.90 (s, 3H, -NCH3), 2.66 (s, 3H, -CH3), 2.61 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 161.11,
159.75, 158.47, 157.28, 150.80, 146.57, 136.62, 128.77, 128.43, 108.51,
33.76, 23.32, 13.53.
[0108] 化合物91：1H NMR (500 MHz, Chloroform-D) δ 9.04 (s, 1H), 8.79 (d, J = 2.2 Hz, 1H), 8.02 (d, J = 8.4 Hz, 1H), 7.95 (dd, J = 8.4, 2.2 Hz, 1H), 3.90 (s, 3H), 2.61 (s, 3H), 2.57 (s, 3H); 13C NMR (125 MHz, Chloroform-D) δ 168.90,
165.14, 157.14, 151.38, 150.64, 146.62, 139.48, 135.92, 123.63, 122.87,
102.63, 33.75, 23.28, 13.53.
165.14, 157.14, 151.38, 150.64, 146.62, 139.48, 135.92, 123.63, 122.87,
102.63, 33.75, 23.28, 13.53.
[0109] 化合物92：1H NMR (500 MHz, Chloroform-D) δ 9.74 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.78 (d,Hz, 1H, pyridine-H), 8.27 (s,1H, -CH=N-), 7.95 (dd, J = 8.4, 2.0 Hz, 1H, pyridine-H), 7.92 (dd, J = 8.4, 2.0 Hz, 1H, pyridine-H), 13
3.94 (s, 3H, -NCH3), 2.59 (s, 3H -CH3); C NMR (125 MHz, Chloroform-D) δ
160.63, 156.75, 151.47, 150.87, 150.29, 149.64, 146.99, 139.51, 123.33,
123.24, 104.25, 77.36, 77.11, 76.86, 34.04, 13.66.
3.94 (s, 3H, -NCH3), 2.59 (s, 3H -CH3); C NMR (125 MHz, Chloroform-D) δ
160.63, 156.75, 151.47, 150.87, 150.29, 149.64, 146.99, 139.51, 123.33,
123.24, 104.25, 77.36, 77.11, 76.86, 34.04, 13.66.
[0110] 化合物93：1H NMR (500 MHz, Chloroform-D) δ 9.86 (s, 1H, pyrazolo[3,4-4
d]pyrimidine-H), 8.81 (d, J = 1.1 Hz, 1H, pyridine-H), 8.77 (d, J = 2.2 Hz,
1H, pyridine-H), 8.37 (s, 1H, pyridine-H), 8.25 (s, 1H, -NCH3), 3.94 (s, 3H, -NCH3), 2.59 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 157.25, 156.51,
153.59, 150.21, 149.84, 148.53, 146.96, 136.38, 131.11, 121.44, 104.20,
77.37, 77.12, 76.87, 34.06, 13.66.
d]pyrimidine-H), 8.81 (d, J = 1.1 Hz, 1H, pyridine-H), 8.77 (d, J = 2.2 Hz,
1H, pyridine-H), 8.37 (s, 1H, pyridine-H), 8.25 (s, 1H, -NCH3), 3.94 (s, 3H, -NCH3), 2.59 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 157.25, 156.51,
153.59, 150.21, 149.84, 148.53, 146.96, 136.38, 131.11, 121.44, 104.20,
77.37, 77.12, 76.87, 34.06, 13.66.
[0111] 化合物94：1H NMR (500 MHz, Chloroform-D) δ 9.14 (s, 1H, pyridine-H), 8.85 (s,1H, pyridine-H), 8.79 (s, 1H, pyridine-H), 8.37 (s, 1H, -CH=N-), 3.89 (s, 3H, -NCH3), 2.64 (s, 3H, -CH3), 2.62 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 160.49, 158.49, 157.39, 156.03, 153.90, 148.60, 146.60,
136.78, 130.66, 121.43, 102.60, 33.78, 23.41, 13.56.
136.78, 130.66, 121.43, 102.60, 33.78, 23.41, 13.56.
[0112] 化合物95：1H NMR (500 MHz, DMSO-d6) δ 9.74 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.59 (dd, J = 4.7, 2.0 Hz, 1H, pyridine-H), 8.53 (s, 1H, -CH=N-), 8.49 (dd, J = 7.7, 1.9 Hz, 1H, pyridine-H), 7.61 (dd, J = 7.6, 4.7 Hz, 1H, pyridine-H), 3.83 (s, 3H, -NCH3), 2.44 (s, 3H, -CH3).
[0113] 化合物96：1H NMR (500 MHz, DMSO-d6 ) δ 8.61 (dd, J = 14.9, 3.0 Hz, 1H), 8.55 (dd, J = 15.0, 3.1 Hz, 1H), 8.35 (s, 1H), 7.84 (d, J = 15.0 Hz,
1H), 4.06 (s, 3H), 2.51 (s, 3H), 1.95 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
164.05, 157.60, 150.88, 149.86, 148.42, 146.93, 146.82, 137.98, 132.17,
123.63, 107.61, 38.34, 20.90, 14.76.
1H), 4.06 (s, 3H), 2.51 (s, 3H), 1.95 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
164.05, 157.60, 150.88, 149.86, 148.42, 146.93, 146.82, 137.98, 132.17,
123.63, 107.61, 38.34, 20.90, 14.76.
[0114] 化合物97：1H NMR (500 MHz, Chloroform-D) δ 9.44 (s, 1H, -CH=N-), 8.54 (dd, J = 4.7, 1.9 Hz, 1H, pyridine-H), 8.47 (dd, J = 7.7, 1.9 Hz, 1H, pyridine-H), 7.39 (dd, J = 7.8, 4.9 Hz, 1H, pyridine-H), 3.91 (s, 3H, -NCH3),
2.61 (s, 3H, -CH3), 2.58 (s, 3H, -CH3). 13C NMR (125 MHz, Chloroform-D) δ
161.13, 157.26, 154.27, 152.55, 146.66, 145.36, 138.13, 136.65, 127.89,
123.04, 101.93, 33.65, 22.74, 13.50, 0.07.
2.61 (s, 3H, -CH3), 2.58 (s, 3H, -CH3). 13C NMR (125 MHz, Chloroform-D) δ
161.13, 157.26, 154.27, 152.55, 146.66, 145.36, 138.13, 136.65, 127.89,
123.04, 101.93, 33.65, 22.74, 13.50, 0.07.
[0115] 化合物98：1H NMR (500 MHz, DMSO-d6 ) δ 9.96 (s, 1H), 8.19 (s, 1H), 7.42 (d, J = 2.9 Hz, 1H), 7.09 (d, J = 3.1 Hz, 1H), 4.07 (s, 3H), 1.97 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 149.86, 149.07, 147.07, 144.43,
135.04, 131.11, 129.31, 110.72, 102.60, 38.34, 14.76.
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 149.86, 149.07, 147.07, 144.43,
135.04, 131.11, 129.31, 110.72, 102.60, 38.34, 14.76.
[0116] 化合物99：1H NMR (500 MHz, DMSO-d6 ) δ 9.32 (d, J = 1.3 Hz, 1H), 8.94 (dd, J = 7.5, 1.4 Hz, 1H), 8.77 (d, J = 1.3 Hz, 1H), 8.40 (t, J = 1.5 Hz, 1H), 8.36 (s, 1H), 7.84 (t, J = 7.5 Hz, 1H), 7.20 (dd, J = 7.4, 1.5 Hz, 1H),
2.51 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 159.75,
157.75, 154.71, 153.62, 150.43, 149.36, 148.96, 148.13, 140.57, 139.18,
136.72, 127.96, 125.46, 117.25, 101.39, 20.90, 14.77.
2.51 (s, 3H), 1.93 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 159.75,
157.75, 154.71, 153.62, 150.43, 149.36, 148.96, 148.13, 140.57, 139.18,
136.72, 127.96, 125.46, 117.25, 101.39, 20.90, 14.77.
[0117] 化合物100：1H NMR (500 MHz, DMSO-d6 ) δ 8.93 (dd, J = 15.0, 3.1 Hz, 1H), 8.61 (dd, J = 14.9, 3.0 Hz, 1H), 8.55 (dd, J = 15.0, 3.1 Hz, 1H), 8.35 (s, 1H), 8.18 (s, 1H), 7.84 (q, J = 14.9 Hz, 2H), 7.19 (dd, J = 14.9, 3.0 Hz,
1H), 1.94 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62,
151.83, 148.96, 148.42, 147.70, 146.82, 143.15, 139.18, 137.98, 132.17,
127.96, 125.46, 123.63, 101.11, 14.79.
1H), 1.94 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62,
151.83, 148.96, 148.42, 147.70, 146.82, 143.15, 139.18, 137.98, 132.17,
127.96, 125.46, 123.63, 101.11, 14.79.
[0118] 化合物101：1H NMR (500 MHz, DMSO-d6 ) δ 8.93 (dd, J = 15.0, 2.9 Hz, 1H), 8.61 (dd, J = 14.9, 3.0 Hz, 1H), 8.55 (dd, J = 15.0, 2.9 Hz, 1H), 8.35 (s, 1H), 7.85 (q, J = 14.9 Hz, 2H), 7.19 (dd, J = 15.0, 3.1 Hz, 1H), 2.51 (s,
3H), 1.67(s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 157.75, 154.71, 153.62,
150.88, 149.36, 148.96, 148.42, 146.82, 139.18, 137.98, 132.17, 127.96,
125.46, 123.63, 101.39, 20.90, 14.73.
3H), 1.67(s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 157.75, 154.71, 153.62,
150.88, 149.36, 148.96, 148.42, 146.82, 139.18, 137.98, 132.17, 127.96,
125.46, 123.63, 101.39, 20.90, 14.73.
[0119] 化合物102：1H NMR (500 MHz, DMSO-d6 ) δ 9.95 (s, 1H), 8.93 (dd, J = 15.0, 2.9 Hz, 1H), 8.18 (s, 1H), 7.83 (t, J = 15.0 Hz, 1H), 7.31 (d, J = 3.1 Hz, 1H), 7.19 (dd, J = 14.9, 3.0 Hz, 1H), 7.09 (d, J = 2.9 Hz, 1H), 1.97 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62, 149.07, 148.96,
147.70, 143.15, 139.18, 135.04, 131.11, 129.31, 127.96, 125.46, 110.72,
101.11, 14.76.
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62, 149.07, 148.96,
147.70, 143.15, 139.18, 135.04, 131.11, 129.31, 127.96, 125.46, 110.72,
101.11, 14.76.
[0120] 化合物103：1H NMR (500 MHz, DMSO-d6 ) δ 9.96 (s, 1H), 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.87 – 7.78 (m, 2H), 7.74 (dd, J = 15.0, 3.1 Hz, 1H), 7.20 (ddd, J = 15.0, 9.0, 6.0 Hz, 2H), 1.97(s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62, 148.96, 147.75, 147.70, 143.15, 139.18,
138.33, 129.68, 128.67, 127.96, 126.34, 125.46, 101.11, 14.77.
138.33, 129.68, 128.67, 127.96, 126.34, 125.46, 101.11, 14.77.
[0121] 化合物104：1H NMR (500 MHz, DMSO-d6 ) δ 9.96 (s, 1H), 8.94 (dd, J = 7.5, 1.4 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H), 7.81 (dd, J = 7.5, 1.4 Hz, 1H),
7.74 (dd, J = 7.4, 1.5 Hz, 1H), 7.20 (ddd, J = 7.5, 4.5, 3.0 Hz, 2H), 2.59 (s, 3H), 1.95 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 157.75, 154.71,
153.62, 149.36, 148.96, 143.50, 139.18, 138.33, 129.68, 128.67, 127.96,
126.34, 125.46, 101.39, 20.90, 14.75.
7.74 (dd, J = 7.4, 1.5 Hz, 1H), 7.20 (ddd, J = 7.5, 4.5, 3.0 Hz, 2H), 2.59 (s, 3H), 1.95 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 157.75, 154.71,
153.62, 149.36, 148.96, 143.50, 139.18, 138.33, 129.68, 128.67, 127.96,
126.34, 125.46, 101.39, 20.90, 14.75.
[0122] 化合物105：1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.28 (s, 1H), 8.19 (s, 2H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J =
15.0, 2.9 Hz, 1H), 6.95 (dd, J = 14.9, 3.0 Hz, 1H), 6.51 (dd, J = 15.0, 3.1 Hz, 1H), 6.15 (t, J = 14.9 Hz, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
163.25, 154.71, 153.62, 148.96, 147.70, 147.53, 143.15, 139.18, 127.96,
126.26, 125.46, 122.79, 116.16, 110.32, 101.11, 14.76.
15.0, 2.9 Hz, 1H), 6.95 (dd, J = 14.9, 3.0 Hz, 1H), 6.51 (dd, J = 15.0, 3.1 Hz, 1H), 6.15 (t, J = 14.9 Hz, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ
163.25, 154.71, 153.62, 148.96, 147.70, 147.53, 143.15, 139.18, 127.96,
126.26, 125.46, 122.79, 116.16, 110.32, 101.11, 14.76.
[0123] 化合物106：1H NMR (500 MHz, DMSO-d6 ) δ 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 8.11 (s, 1H), 7.83 (d, J = 15.0 Hz, 1H), 7.21 – 7.13 (m,
1H), 6.96 – 6.88 (m, 1H), 6.51 (dd, J = 15.0, 3.1 Hz, 1H), 6.15 (t, J = 14.9 Hz, 1H), 2.48 (s, 3H), 1.92 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05,
157.75, 154.71, 153.62, 149.36, 148.96, 147.76, 139.18, 127.96, 126.26,
125.46, 122.79, 116.16, 110.32, 101.39, 20.90, 14.79.
1H), 6.96 – 6.88 (m, 1H), 6.51 (dd, J = 15.0, 3.1 Hz, 1H), 6.15 (t, J = 14.9 Hz, 1H), 2.48 (s, 3H), 1.92 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05,
157.75, 154.71, 153.62, 149.36, 148.96, 147.76, 139.18, 127.96, 126.26,
125.46, 122.79, 116.16, 110.32, 101.39, 20.90, 14.79.
[0124] 化合物107：1H NMR (500 MHz, DMSO-d6 ) δ 9.96 (s, 1H), 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz,
1H), 7.08 (d, J = 15.0 Hz, 1H), 6.64 (d, J = 15.0 Hz, 1H), 2.52 (s, 3H), 2.47 (s, 3H), 1.83 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 157.75, 154.71,
153.62, 149.36, 148.96, 143.91, 142.00, 139.18, 138.53, 127.96, 127.18,
126.53, 125.46, 101.39, 20.90, 17.13, 14.73.
1H), 7.08 (d, J = 15.0 Hz, 1H), 6.64 (d, J = 15.0 Hz, 1H), 2.52 (s, 3H), 2.47 (s, 3H), 1.83 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 164.05, 157.75, 154.71,
153.62, 149.36, 148.96, 143.91, 142.00, 139.18, 138.53, 127.96, 127.18,
126.53, 125.46, 101.39, 20.90, 17.13, 14.73.
[0125] 化合物108：1H NMR (500 MHz, DMSO-d6 ) δ 9.96 (s, 1H), 8.94 (dd, J = 15.0, 2.9 Hz, 1H), 8.19 (s, 1H), 7.84 (t, J = 15.0 Hz, 1H), 7.42 (d, J = 2.9 Hz, 1H), 7.20 (dd, J = 15.0, 2.9 Hz, 1H), 7.09 (d, J = 3.1 Hz, 1H), 1.98 (s,
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62, 149.07, 148.96,
147.70, 143.15, 139.18, 135.04, 131.11, 129.31, 127.96, 125.46, 110.72,
101.11, 14.98.
3H); 13C NMR (125 MHz, DMSO-d6) δ 163.25, 154.71, 153.62, 149.07, 148.96,
147.70, 143.15, 139.18, 135.04, 131.11, 129.31, 127.96, 125.46, 110.72,
101.11, 14.98.
[0126] 化合物109：1H NMR (500 MHz, DMSO-d6) δ 8.38 (s, 1H, -CH=N-)), 7.14 (s, 1H, thiophene-H), 6.74 (s, 1H, thiophene-H), 6.24 (dd, J = 5.8, 2.4 Hz, 1H, thiophene-H), 3.77 (s, 3H, -NCH3), 2.52 (s, 3H, -CH3), 2.44 (s, 3H, -CH3); 13C NMR (125 MHz, DMSO-d6) δ 158.81, 157.55, 155.32, 150.66, 145.53, 144.59,
143.82, 125.92, 118.94, 101.68, 40.51, 40.34, 40.18, 40.01, 39.84, 39.68,
39.51, 33.80, 23.00, 13.61.
143.82, 125.92, 118.94, 101.68, 40.51, 40.34, 40.18, 40.01, 39.84, 39.68,
39.51, 33.80, 23.00, 13.61.
[0127] 化合物110：1H NMR (500 MHz, Chloroform-D) δ 9.72 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.21 (s, 1H, -CH=N-), 7.55 (d, J = 5.0 Hz, 1H, thiophene-H), 7.49 (s, 1H, thiophene-H), 7.14 (dt, J = 5.2, 3.1 Hz, 1H, , thiophene-H),
3.93 (s, 3H, -NCH3), 2.65 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ
156.93, 150.50, 149.23, 146.65, 137.88, 134.10, 131.18, 128.03, 104.27,
33.99, 13.65.
3.93 (s, 3H, -NCH3), 2.65 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ
156.93, 150.50, 149.23, 146.65, 137.88, 134.10, 131.18, 128.03, 104.27,
33.99, 13.65.
[0128] 化合物111：1H NMR (500 MHz, Chloroform-D) δ 9.36 (s, 1H, -NH), 9.01 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.12 (s, 1H, -CH=N-), 7.05 (s, 1H, pyrrole-H), 6.72 (d, 4J = 1.7 Hz, 1H, pyrrole-H), 6.33 (dd, 3J = 5.9, 4J = 2.7 Hz, 1H, pyrrole-H), 3.91 (s, 3H -NCH3), 2.52 (s, 3H -CH3); 13C NMR (125 MHz, Chloroform-D) δ 156.42, 154.66, 150.75, 148.11, 146.47, 126.14, 124.14, 118.85, 111.16, 104.33, 33.93, 13.64.
[0129] 化合物112：1H NMR (500 MHz, Chloroform-D) δ 9.07 (s, 1H, -CH=N-), 7.57 (d, 3J = 5.1 Hz, 1H, pyrrole-H), 7.51 (d, 4J = 3.5 Hz, 1H, pyrrole-H), 7.15 (dd, 3J = 5.0, 4J = 3.6 Hz, 1H, pyrrole-H), 3.89 (s, 3H, -NCH3), 2.60 (s, 3H, -CH3), 2.57 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 159.81, 157.26, 156.06, 150.30, 146.32, 137.53, 134.27, 131.53, 128.04, 102.67, 33.71, 23.21,
13.54.
13.54.
[0130] 化合物113：1H NMR (500 MHz, Chloroform-D) δ 9.82 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.68 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.23 (s, 1H, -CH=N-), 8.06 (d, J = 8.2 Hz, 1H, thiophene-H), 7.60 (d, J = 8.2 Hz, 1H, thiophene-H), 3.94 (s, 3H, -NCH3), 2.59 (s, 3H, -CH3); 13C NMR (125 MHz, Chloroform-D) δ 157.31, 157.16, 150.68, 150.27, 149.68, 146.92, 145.55,
136.31, 128.85, 128.72, 104.21, 77.36, 77.10, 76.85, 34.04, 13.64.
136.31, 128.85, 128.72, 104.21, 77.36, 77.10, 76.85, 34.04, 13.64.
[0131] 化合物114： 1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.6, 2.2 Hz, 1H), 8.37 (dd, J = 3.3, 1.5 Hz, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 7.93 – 7.85 (m, 4H), 7.83 (dd, J = 10.7, 7.4 Hz, 1H), 7.49 – 7.41 (m, 2H), 7.15 (s, 1H);
13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 151.32, 144.50, 141.17, 140.69,
137.42, 131.97, 129.30, 129.07, 127.21, 125.96, 125.47, 123.62, 85.79.
13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 151.32, 144.50, 141.17, 140.69,
137.42, 131.97, 129.30, 129.07, 127.21, 125.96, 125.47, 123.62, 85.79.
[0132] 化合物115：1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.37 (dd, J = 3.3, 1.5 Hz, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 7.94 – 7.79 (m, 5H), 7.15 (s, 1H), 7.14 – 7.08 (m, 2H), 3.79 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 161.04, 159.91, 156.07, 151.32, 144.50, 141.17, 140.69, 129.30,
129.07, 128.59, 127.22, 125.47, 114.03, 85.79, 56.08.
129.07, 128.59, 127.22, 125.47, 114.03, 85.79, 56.08.
[0133] 化合物116：1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (d, J = 1.2 Hz, 1H), 8.37 (d, J = 1.3 Hz, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 7.94 – 7.86 (m, 4H), 7.85 – 7.77 (m, 1H), 7.15 (s, 1H), 7.05 (d, J = 7.5 Hz, 2H); 13C NMR (125 MHz, DMSO-d6) δ 161.04, 156.07, 151.32, 150.43, 144.50, 141.17, 140.69, 130.16, 129.30,
129.07, 129.02, 125.47, 121.36, 120.42, 85.79.
129.07, 129.02, 125.47, 121.36, 120.42, 85.79.
[0134] 化合物117：1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.36 (dt, J = 6.6, 3.4 Hz, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 8.11 (t, J =
13.9 Hz, 1H), 7.93 – 7.77 (m, 3H), 2.34 (q, J = 14.5 Hz, 2H), 1.55 (ddt, J =
25.3, 14.5, 10.4 Hz, 2H), 1.48 – 1.29 (m, 2H), 0.93 (t, J = 13.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.53, 156.07, 151.32, 144.50, 141.17, 140.69,
129.30, 129.07, 125.47, 85.79, 32.29, 30.45, 22.08, 14.00.
13.9 Hz, 1H), 7.93 – 7.77 (m, 3H), 2.34 (q, J = 14.5 Hz, 2H), 1.55 (ddt, J =
25.3, 14.5, 10.4 Hz, 2H), 1.48 – 1.29 (m, 2H), 0.93 (t, J = 13.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 168.53, 156.07, 151.32, 144.50, 141.17, 140.69,
129.30, 129.07, 125.47, 85.79, 32.29, 30.45, 22.08, 14.00.
[0135] 化合物118：1H NMR (500 MHz, DMSO-d6 ) δ 8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.38 – 8.34 (m, 2H), 8.22 (s, 1H), 8.19 (s, 1H), 7.96 – 7.85 (m, 2H),
7.85 – 7.76 (m, 2H), 7.63 (td, J = 14.8, 9.8 Hz, 1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.44 (ddt, J = 15.9, 14.7, 3.2 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) δ
162.82, 162.46, 156.07, 151.32, 144.50, 141.17, 140.69, 136.54, 130.26,
129.30, 129.07, 125.47, 125.06, 115.79, 114.83, 85.79.
7.85 – 7.76 (m, 2H), 7.63 (td, J = 14.8, 9.8 Hz, 1H), 7.53 (dt, J = 14.9, 3.1 Hz, 1H), 7.44 (ddt, J = 15.9, 14.7, 3.2 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) δ
162.82, 162.46, 156.07, 151.32, 144.50, 141.17, 140.69, 136.54, 130.26,
129.30, 129.07, 125.47, 125.06, 115.79, 114.83, 85.79.
[0136] 本发明的化合物制备的植物病毒抑制剂，主要包括烟草、黄瓜、番茄、辣椒、水稻、马铃薯等作物；主要的病毒包括烟草花叶病毒、马铃薯Y病毒、马铃薯X病毒、马铃薯S病毒、马铃薯A病毒、黄瓜花叶病毒、番茄病毒病、辣椒病毒病、水稻病毒病等。
具体实施方式
[0137] 以抗烟草花叶病毒（Tobacco Mosaic Virus，TMV）及黄瓜花叶病毒病（CNV）的活性为例，但并不限定本发明化合物抗其它病毒的应用。
[0138] 实施例1：对烟草花叶病（TMV）的活体保护作用
[0139] 选取长势一致5-6叶期的心叶烟，用毛笔轻轻在左半叶涂施药剂，右半叶涂施对应剂量的溶剂作对照。在光照培养箱中保湿培养，控制温度23±1 ℃，光照10000 Lux，12 h后用磷酸缓冲液将TMV病毒液稀释至适宜浓度，用排笔人工摩擦接种于撒有金刚砂的叶片上，全叶接种病毒，自然晾干后清水冲洗叶片。随后在光照培养箱中保湿培养，控制温度23±1 ℃，光照10000 Lux 。每药剂处理设3株，每株3 4片叶。按上述方法每药剂进行3次重复。~
[0140] 结果调查与分析：参照文献（Fan Z.J.;et al.J.Agric.Food Chem.，2010，58(5):2630-2636和Zuo X.;et al.J.Agric. Food Chem.，2010，58(5):2755-2762）等所描述的方法进行化合物对烟草花叶病毒的保护评价。当空白对照的半叶上呈现明显枯斑，约在实验
2-3 d后就可调查，分别记录每片叶的左右半叶的枯斑数，按下列计算出供试化合物对烟草花叶病毒的抑制率，即相对效果。
2-3 d后就可调查，分别记录每片叶的左右半叶的枯斑数，按下列计算出供试化合物对烟草花叶病毒的抑制率，即相对效果。
[0141] Y=(C-A) ∕ C ×100%
[0142] 其中：Y 为化合物对对烟草花叶病毒的抑制率；
[0143] C 为对照组(右半叶) 枯斑数，单位：个；
[0144] A 为化合物处理组(左半叶) 枯斑数，单位：个。
[0145] 对照组(右半叶) 枯斑数和化合物处理组(左半叶) 枯斑数都可以参用各组重复的平均数或各组重复的枯斑总数。每个处理都是用自己的另一半作为对照。部分化合物的活性结果结果如表2。
[0146] 当空白对照的半叶上呈现明显枯斑，约在实验2-3 d后就可调查，分别记录每片叶的左右半叶的枯斑数，按下列计算出供试化合物对烟草花叶病毒的抑制率，即相对效果。
[0147] Y=(C-A) ∕ C ×100%
[0148] 其中：Y 为化合物对对烟草花叶病毒的抑制率；
[0149] C 为对照组(右半叶) 枯斑数，单位：个；
[0150] A 为化合物处理组(左半叶) 枯斑数，单位：个。
[0151] 对照组(右半叶) 枯斑数和化合物处理组(左半叶) 枯斑数都可以参用各组重复的平均数或各组重复的枯斑总数。每个处理都是用自己的另一半作为对照。部分化合物的活性结果结果如表2.
[0152]
[0153] 对烟草花叶病（TMV）的钝化作用
[0154] 选取长势一致的5-6叶期的心叶烟，用磷酸缓冲液将TMV病毒液稀释至6×10-3 mg ∕ mL，将药剂与等体积的病毒汁液混合钝化30 min，用排笔人工摩擦接种于撒有金刚砂的左半叶，对应剂量的溶剂与病毒汁液混合接种右半叶，自然晾干后用清水冲洗。随后在光照培养箱中保湿培养，控制温度23±1 ºC，光照10000 Lux，2-3 d后观察并记录产生枯斑的数目。每药剂处理设3株，每株3 4片叶。按上述方法每药剂进行3次重复。~
[0155] 结果调查与分析：参照文献（Fan Z.J.;et al.J.Agric.Food Chem.，2010，58(5):2630-2636和Zuo X.;et al.J.Agric. Food Chem.，2010，58(5):2755-2762）等所描述的方法进行化合物对烟草花叶病毒的钝化进行评价。当空白对照的半叶上呈现明显枯斑，约在实验2-3 d后就可调查，分别记录每片叶的左右半叶的枯斑数，按下列计算出供试化合物对烟草花叶病毒的抑制率，即相对效果。
[0156] Y=(C-A) ∕ C ×100%
[0157] 其中：Y 为化合物对对烟草花叶病毒的抑制率；
[0158] C 为对照组(右半叶) 枯斑数，单位：个；
[0159] A 为化合物处理组(左半叶) 枯斑数，单位：个。
[0160] 对照组(右半叶) 枯斑数和化合物处理组(左半叶) 枯斑数都可以参用各组重复的平均数或各组重复的枯斑总数。每个处理都是用自己的另一半作为对照。部分化合物的活性结果结果如表3所示。
[0161]
[0162]
[0163] 对烟草花叶病（TMV）的活体治疗作用
[0164] 选长势一致的5-6叶期的心叶烟，用磷酸缓冲液将TMV病毒液稀释至适宜的浓度，全叶撒匀金刚砂，用排笔全叶接种病毒，自然晾干后用清水冲洗。待叶片干后，在左半叶用毛笔涂施药剂，右半叶涂施对应剂量的溶剂作对照。随后在光照培养箱中保湿培养，控制温度23±1 ºC，光照10000 Lux，2-3 d后观察并记录产生枯斑的数目。每药剂处理设3株，每株3 4片叶。按上述方法每药剂进行3次重复。
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[0165] 结果调查与分析：参照文献（Fan Z.J.;et al.J.Agric.Food Chem.，2010，58(5):2630-2636和Zuo X.;et al.J.Agric. Food Chem.，2010，58(5):2755-2762）等所描述的方法进行化合物对烟草花叶病毒的治疗作用进行评价。当空白对照的半叶上呈现明显枯斑，约在实验2-3d后就可调查，分别记录每片叶的左右半叶的枯斑数，按下列计算出供试化合物对烟草花叶病毒的抑制率，即相对效果。
[0166] Y=(C-A) ∕ C ×100%
[0167] 其中：Y 为化合物对对烟草花叶病毒的抑制率；
[0168] C 为对照组(右半叶) 枯斑数，单位：个；
[0169] A 为化合物处理组(左半叶) 枯斑数，单位：个。
[0170] 对照组(右半叶) 枯斑数和化合物处理组(左半叶) 枯斑数都可以参用各组重复的平均数或各组重复的枯斑总数。每个处理都是用自己的另一半作为对照。部分化合物的活性结果结果如表4所示。
[0171]
[0172] 实施例2：抗黄瓜花叶病毒活体保护活性
[0173] 采用文献（华南农业大学学报, 1995, 16: 74-79）所描述的半叶枯斑法，对所合成的化合物进行了抗 CMV 生物活性测试。
[0174] 选取长势一致的苋色藜，用毛笔轻轻在左半叶涂施药剂，右半叶涂施灭菌水作对照，24 小时后接种病毒。用排笔蘸取病毒汁液（浓度为 6×10-3 mg / mL），在叶面（全叶）沿其支脉方向人工摩擦接种于撒有金刚砂的叶片上，左右叶片的接种力度尽量保持一致，叶片下方用平整木板支撑。待病毒液干后，用流水冲洗掉叶片上面的金刚砂。每药剂处理设 3 株，每株 5-6 片叶，随后将植株放在光照培养箱中保湿培养，控制温度 23±1°C，光照 10000 Lux，6-7 d 后观察并记录产生枯斑的数目。按上述方法每药剂进行 3 次重复，计算抑制率。
[0175]
[0176] 部分测试结果如下：
[0177] 在浓度为500 mg/L时：化合物1、2、5、8、10、14、15、18、26、29、30、32、33、45、49、50、51、54、55、57、50、61、62、64、65、68、69、70、71、72、73、75的抑制率为83%；化合物77的抑制率为68%；化合物79的抑制率为86%；化合物81的抑制率为87%；化合物91的抑制率为92%；化合物113的抑制率为85%；化合物117的抑制率为82%；化合物118的抑制率为79%；
[0178] 抗黄瓜花叶病毒活体治疗活性
[0179] 选取长势一致的苋色藜，先用排笔蘸取病毒液（浓度为 6×10-3 mg / mL），在叶面（全叶）沿其支脉方向人工摩擦接种于撒有金刚砂的叶片上，左右叶片的接种力度尽量保持一致，叶片下方用平整木板支撑。待病毒液干后，用流水冲洗掉叶片上面的金刚砂。待叶片干后，在左半叶涂施药剂，右半叶涂施灭菌水作对照。每药剂处理设 3 株，每株 5-6 片叶，随后将植株放在光照培养箱中保湿培养，控制温度 23±1 °C，光照 10000 Lux，6-7 d 后观察并记录产生枯斑的数目。按上述方法每药剂进行 3 次重复，计算抑制率。
[0180]
[0181] 部分测试结果如表5所示：
[0182]
[0183] 对CMV侵染的活体钝化作用
[0184] 将药剂与等体积的病毒汁液混合钝化 30 min，用排笔蘸取药剂与病毒的混合液，人工摩擦接种于撒有金刚砂的叶片左半边叶片上，叶片下方用平整木板支撑。灭菌水与病毒汁液混合接种右半叶。每药剂处理设 3 株，每株 5-6 片叶，随后将植株放在光照培养箱中保湿培养，控制温度 23±1 °C，光照 10000 Lux，6-7 d 后观察并记录产生枯斑的数目。按上述方法每药剂进行 3 次重复，计算抑制率。
[0185]
[0186] 所得部分化合物的结果如表6所示：
[0187]
[0188] 以上所述，仅是本发明的较佳实施例而已，并非对本发明作任何形式上的限制，任何未脱离本发明技术方案内容，依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰，均仍属于本发明技术方案的范围内。