CN106070266B - 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 - Google Patents

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 Download PDF

Info

Publication number
CN106070266B
CN106070266B CN201610490135.XA CN201610490135A CN106070266B CN 106070266 B CN106070266 B CN 106070266B CN 201610490135 A CN201610490135 A CN 201610490135A CN 106070266 B CN106070266 B CN 106070266B
Authority
CN
China
Prior art keywords
nmr
mhz
dmso
compound
chloroform
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201610490135.XA
Other languages
English (en)
Other versions
CN106070266A (zh
Inventor
吴剑
徐方舟
薛伟
宋宝安
刘登曰
陈吉祥
胡德禹
杨松
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Guizhou University
Original Assignee
Guizhou University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Guizhou University filed Critical Guizhou University
Priority to CN201610490135.XA priority Critical patent/CN106070266B/zh
Publication of CN106070266A publication Critical patent/CN106070266A/zh
Application granted granted Critical
Publication of CN106070266B publication Critical patent/CN106070266B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

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。

Description

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
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
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(CN1036766)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（Molecules2014, 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
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。
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。
尤其是在抗烟草花叶病毒、黄瓜花叶病毒中的应用。
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：
I
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。
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.
更进一步地，通式I所述的化合物中，较为优选的取代基为：
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.
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：
反应式中，中间体及化合物的取代基于上述相同。
所合成得到的部分目标化合物核磁数据如下：
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, -C H =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.
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.
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, -C H =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.
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.
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) δ165.69, 156.07, 148.17, 145.11, 136.77, 133.23, 130.43, 129.52, 129.18,129.07, 127.60, 85.62, 37.40.
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.
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 (125MHz, 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.
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..
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,1H), 7.20 (dd, J = 15.0, 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, 135.79, 132.84,130.24, 128.06, 127.88, 124.76, 124.40, 124.28, 123.30, 98.23.
化合物10：1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.15 (s, 1H),7.97 – 7.82 (m, 2H), 7.55 – 7.40 (m, 2H), 7.15 (s, 1H), 3.96 (s, 3H). 13C 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.
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.
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.
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.
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.
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),7.15 (s, 1H); 13C 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.
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.
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.
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 = 15.0Hz, 1H), 7.20 (dd, J = 14.9, 3.0 Hz, 1H); 13C 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.
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.
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.
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.
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.
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.
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,
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.
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,1H), 7.00 – 6.85 (m, 2H), 4.07 (s, 3H), 1.98 (s, 3H); 13C 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.
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.
化合物28: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.08 (t, J = 14.0Hz, 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.
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.
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.
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.
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.
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).; 13CNMR (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.
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.
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.
化合物36: 1H NMR (500 MHz, DMSO-d6 ) δ 8.19 (s, 1H), 8.07 (t, J = 13.9Hz, 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.
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.
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.
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); 13CNMR (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.
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.
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, 3.4Hz, 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.
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.
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, 3.1Hz, 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.
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.
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.
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); 13CNMR (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.
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.
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.
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, -C H =N), 7.61 – 7.53 (m, 1H, pyridine-H), 3.92 (s,3H, -NCH3); 13C 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):ν3444.8, 3041.7, 1693.5, 1593.2, 1568.1, 1541.1, 1145.7 cm-1
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, -C H =N), 3.91 (s, 3H, -NCH3), 2.55 (s, 3H, -CH3); 13C NMR (125MHz, 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, 1593.2,1568.1, 1541.1, 1145.7 cm-1.
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, -C H =N),8.03 (d, 4 J = 1.5 Hz, 1H, furan-H), 7.27 (d, 1H, 3 J = 3.5 Hz, furan-H), 6.75(dd, 3 J = 3.5, 4 J =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.
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, -C H =N), 3.91 (s, 3H, -NCH3), 3.78 (s, 3H, -NCH3), 2.37 (s, 3H, -CH3). 13C NMR (125MHz, 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.
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.
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 (125MHz, 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.
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.
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) δ163.25, 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.
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.
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); 13CNMR (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.
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 (125MHz, 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.
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.
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,J = 15.3, 3.0 Hz, 2H), 7.94 – 7.76 (m, 3H), 7.72 (t, J = 14.9 Hz, 1H); 13C 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.
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.
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.
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.
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, 2.9Hz, 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.
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.
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.
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) δ156.07, 148.17, 147.53, 145.11, 136.77, 126.26, 122.79, 116.16, 110.32,85.62, 37.40.
化合物70： 1H NMR (500 MHz, DMSO-d6) δ 9.33 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.77 (dd, 3 J = 4.4 Hz, 4 J = 1.5 Hz, 1H, pyridine-H), 8.74 (dd,3 J = 4.4 Hz, 4 J = 1.5 Hz, 1H, pyridine-H), 8.60 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.17 (s, 1H, -C H =N), 7.82 (dd, 3 J = 4.5 Hz, 4 J = 1.5 Hz, 1H,pyridine-H), 7.77 (dd, 3 J = 4.3 Hz, 4 J = 1.5 Hz, 1H, pyridine-H); 13C NMR (125MHz, DMSO-d6) δ 163.63, 151.25, 151.17, 148.96, 140.19, 135.58, 123.28,122.56, 105.97, 34.70.
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, -C H =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.
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, -C H =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.
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 (125MHz, Chloroform-D) δ 157.06, 155.14, 148.01, 146.92, 135.44, 118.94, 112.64,104.63, 34.18, 23.23.
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, -C H =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.
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(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.
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, -C H =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).
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
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.
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.
化合物81：1H NMR (500 MHz, Chloroform-D) δ 8.87 (s, 1H,-C H =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;
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,-C H =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.
化合物83：1H NMR (500 MHz, Chloroform-D) δ 8.47 (s, 1H, -C H =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.
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.
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.
化合物86：1H NMR (500 MHz, Chloroform-D) δ 8.84 (s, 1H, -C H =N-), 7.84(d, 4 J = 2.8 Hz, 1H, thiophene-H), 7.67 (d, 3 J = 5.0 Hz, 1H, thiophene-H),7.42 (dd, 3 J = 5.0, 4 J = 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.
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, -C H =N-), 7.80 (d, 4 J = 2.3 Hz, 1H, thiophene-H), 7.63 (d, 3 J = 5.2 Hz, 1H, thiophene-H), 7.41 (dd, 3 J = 5.1, 4 J = 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.
化合物88：1H NMR (500 MHz, Chloroform-D) δ 8.89 (s, 1H, -C H =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).13C 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.
化合物89：1H NMR (500 MHz, Chloroform-D) δ 9.52 (s, 1H, pyridine-H),8.18 (s, 1H, -C H =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.
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.
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.
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, -C H =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),3.94 (s, 3H, -NCH3), 2.59 (s, 3H -CH3); 13C NMR (125 MHz, Chloroform-D) δ160.63, 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.
化合物93：1H NMR (500 MHz, Chloroform-D) δ 9.86 (s, 1H, pyrazolo[3,4-d]pyrimidine-H), 8.81 (d, 4 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.
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, -C H =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.
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, -C H =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).
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) δ164.05, 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.
化合物97：1H NMR (500 MHz, Chloroform-D) δ 9.44 (s, 1H, -C H =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) δ161.13, 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.
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.
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.
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.
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.
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 = 3.1Hz, 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.
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, 3.1Hz, 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.
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.
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, 3.1Hz, 1H), 6.15 (t, J = 14.9 Hz, 1H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ163.25, 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.
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 = 14.9Hz, 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.
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.
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 = 2.9Hz, 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.
化合物109：1H NMR (500 MHz, DMSO-d6) δ 8.38 (s, 1H, -C H =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); 13CNMR (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.
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, -C H =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) δ156.93, 150.50, 149.23, 146.65, 137.88, 134.10, 131.18, 128.03, 104.27,33.99, 13.65.
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, -C H =N-), 7.05 (s, 1H,pyrrole-H), 6.72 (d, 4 J = 1.7 Hz, 1H, pyrrole-H), 6.33 (dd, 3 J = 5.9, 4 J = 2.7Hz, 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.
化合物112：1H NMR (500 MHz, Chloroform-D) δ 9.07 (s, 1H, -C H =N-), 7.57(d, 3 J = 5.1 Hz, 1H, pyrrole-H), 7.51 (d, 4 J = 3.5 Hz, 1H, pyrrole-H), 7.15(dd, 3 J = 5.0, 4 J = 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.
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, -C H =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.
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.
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.
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.
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); 13CNMR (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.
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, 3.1Hz, 1H), 7.44 (ddt, J = 15.9, 14.7, 3.2 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) δ162.82, 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.
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
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。
实施例1：对烟草花叶病（TMV）的活体保护作用
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。
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。
Y=(C-A) ∕ C ×100%
其中：Y 为化合物对对烟草花叶病毒的抑制率；
C 为对照组(右半叶) 枯斑数，单位：个；
A 为化合物处理组(左半叶) 枯斑数，单位：个。
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。
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。
Y=(C-A) ∕ C ×100%
其中：Y 为化合物对对烟草花叶病毒的抑制率；
C 为对照组(右半叶) 枯斑数，单位：个；
A 为化合物处理组(左半叶) 枯斑数，单位：个。
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.
对烟草花叶病（TMV）的钝化作用
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。
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。
Y=(C-A) ∕ C ×100%
其中：Y 为化合物对对烟草花叶病毒的抑制率；
C 为对照组(右半叶) 枯斑数，单位：个；
A 为化合物处理组(左半叶) 枯斑数，单位：个。
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。
对烟草花叶病（TMV）的活体治疗作用
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。
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。
Y=(C-A) ∕ C ×100%
其中：Y 为化合物对对烟草花叶病毒的抑制率；
C 为对照组(右半叶) 枯斑数，单位：个；
A 为化合物处理组(左半叶) 枯斑数，单位：个。
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。
实施例2：抗黄瓜花叶病毒活体保护活性
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。
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。
部分测试结果如下：
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%；
抗黄瓜花叶病毒活体治疗活性
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。
部分测试结果如表5所示：
对CMV侵染的活体钝化作用
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。
所得部分化合物的结果如表6所示：
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。

Claims (3)

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。
CN201610490135.XA 2016-06-29 2016-06-29 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 Active CN106070266B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610490135.XA CN106070266B (zh) 2016-06-29 2016-06-29 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

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610490135.XA CN106070266B (zh) 2016-06-29 2016-06-29 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

Publications (2)

Publication Number Publication Date
CN106070266A CN106070266A (zh) 2016-11-09
CN106070266B true CN106070266B (zh) 2018-11-30

Family

ID=57215296

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610490135.XA Active CN106070266B (zh) 2016-06-29 2016-06-29 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

Country Status (1)

Country Link
CN (1) CN106070266B (zh)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1036766A (zh) * 1988-03-03 1989-11-01 邻位药品公司 4-取代吡唑[3，4-d]嘧啶衍生物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011507910A (ja) * 2007-12-21 2011-03-10 ユニバーシティー オブ ロチェスター 真核生物の寿命を変更するための方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1036766A (zh) * 1988-03-03 1989-11-01 邻位药品公司 4-取代吡唑[3，4-d]嘧啶衍生物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
NOVEL 4,5-DIHYDROPYRAZOLO[3,4-d]PYRIMIDIN-4-ONES AND 3,4-DIHYDROPYRAZOLO[3,4-d]-1,2,3-TRIAZIN-4-ONES;A. Maquestiau等;《Bull.SOC.Chim.Bdg.》;19911231;第100卷(第5期);第401-406页 *
Synthesis of Some New Pyrazolotriazines,Pyrazolothiazines and Pyrazolopyrimidines;Adel M. Kamal El-Dean等;《J. CHEM. RESEARCH》;19971231;第352-353页 *

Also Published As

Publication number Publication date
CN106070266A (zh) 2016-11-09

Similar Documents

Publication Publication Date Title
DK3129355T3 (en) FUNGICIDE N '- [2-METHYL-6- [2-ALCOXYETHOXY] -3-PYRIDYL] -N-ALKYL FORMAMIDE INGREDIENTS FOR AGRICULTURAL USE
Salem et al. Synthesis, antibacterial, and antiviral evaluation of new heterocycles containing the pyridine moiety
Kalaria et al. Ultrasound-assisted one-pot four-component synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole scaffold and their biological broadcast
US20100222221A1 (en) N-alkoxyamides of 6-(trisubstituted phenyl)-4-aminopicolinates and their use as selective herbicides for crops
JP2006514006A (ja) Ｊａｋインヒビターとしてのヘテロアリール−ピリミジン誘導体
Liu et al. First discovery of novel pyrido [1, 2-a] pyrimidinone mesoionic compounds as antibacterial agents
Devineni et al. 2-Amino-2, 3-dihydro-1 H-2λ 5-[1, 3, 2] diazaphospholo [4, 5-b] pyridin-2-one-based urea and thiourea derivatives: synthesis, molecular docking study and evaluation of anti-inflammatory and antimicrobial activities
CN110526863B (zh) 一种含三氟甲基吡啶的酰基硫脲或酰基脲类衍生物及其应用
JPS6345259A (ja) ピリジン−３−カルボキサミド誘導体
Zhang et al. Synthesis and Antibacterial Activity of 2‐substitued‐(3‐pyridyl)‐quinazolinone Derivatives
DK156721B (da) Substituerede carboxamidforbindelser, fungicide midler indeholdende disse samt anvendelse deraf
CA2846779A1 (en) Plant growth regulating compounds
CN106070266B (zh) 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
CN106070263B (zh) 5-氨基-1H-吡唑[3,4-d]嘧啶-4(5H)-酮类化合物在制备抗植物病毒剂中的应用
CN117263935A (zh) 一种具有除草活性的化合物及其制备方法与应用
CN102285979B (zh) N-(2-(取代苯并噻唑-2-氨基甲酰基)-苯基)-取代吡唑甲酰胺类化合物及其制备方法和用途
CN106588871B (zh) 一种2-取代吡啶基喹唑啉酮类衍生物、其合成方法和用途
ES2642195T3 (es) Compuestos 2-(fenil sustituido)ciclopentan-1,3-diónicos activos como herbicidas y sus derivados
CN111349089A (zh) 一类吲哚杂环化合物及其制备方法和在防治植物病害中的应用
CN115521267A (zh) 一种含n-5-氯异恶唑丙二酸酯结构的苯磺酰胺类化合物、制备方法及用途
CN103951612A (zh) 一种肟醚乙酸酯类化合物及其制备方法与应用
CN110317204B (zh) 吡唑并嘧啶酮类衍生物及其制备方法和应用
CN110452234B (zh) 一种含三氟甲基吡啶二甲酰胺的席夫碱的衍生物及其应用
CN103626652A (zh) 3-芳基丙烯酸及其衍生物抗植物病毒剂
CN106967120B (zh) 含生物碱的磷酸酯类化合物及其制备方法及应用

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant