高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (12): 2759-2765.doi: 10.7503/cjcu20200462

• 有机化学 • 上一篇    下一篇

含1,2,4,5-四取代苯基的吡唑-4-甲酰胺类化合物的设计、 合成及生物活性

董心睿, 夏喆, 王桢学, 边强, 李华斌()   

  1. 南开大学化学学院, 天津 300071
  • 收稿日期:2020-07-16 出版日期:2020-12-10 发布日期:2020-12-09
  • 通讯作者: 李华斌 E-mail:lihuabinnk@163.com
  • 基金资助:
    国家自然科学基金(21102078);“国家级大学生创新创业训练计划”创新训练项目(批准号(201910055090);202010055076)资助

Design, Synthesis and Biological Activity of Pyrazole-4-carboxamides Compounds Containing 1,2,4,5-Tetrasubstituted Phenyl

DONG Xinrui, XIA Zhe, WANG Zhenxue, BIAN Qiang, LI Huabin()   

  1. College of Chemistry,Nankai University,Tianjin 300071,China
  • Received:2020-07-16 Online:2020-12-10 Published:2020-12-09
  • Contact: LI Huabin E-mail:lihuabinnk@163.com
  • Supported by:
    ? Supported by the National Natural Science Foundation of China(21102078);the Innovation Training Program of “National Undergraduate Training Programs for Innovation and Entrepreneurship” of China(201910055090)

摘要:

通过活性亚结构拼接的方法, 设计合成了一系列含四取代苯基的吡唑-4-甲酰胺类化合物, 所有化合物的结构均通过高分辨质谱(HRMS)和核磁共振氢谱(1H NMR)确证. 生物活性测试结果表明, 部分化合物对苹果纹轮病菌、 水稻纹枯病菌、 油菜菌核病菌和黄瓜灰霉病菌表现出较好的杀菌活性. 化合物5c表现出较广的杀菌谱, 在浓度为50 μg/mL时对苹果纹轮病菌的抑制活性高达95.5%. 初步构效关系分析发现, 吡唑环N取代基为甲基或叔丁基时, 化合物表现出较好的活性; 含并环结构的化合物5′杀菌活性低于含单个苯环的化合 物5; 苯环取代基R2为低于4个碳的脂肪链时, 化合物杀菌活性更高.

关键词: 吡唑-4-甲酰胺, 吡唑, 四取代苯, 杀菌活性

Abstract:

To find novel fungicidal compounds with potent biological activities, a series of pyrazole-4-carbo- xamide compounds containing tetra-substituted phenyl groups was designed via the method of linking active sub-structures. The structures of all the compounds were confirmed by high resolution mass spectrometer(HRMS) and hydrogen nuclear magnetic resonance(1H NMR). The bioassay results showed that some compounds have obvious inhibitory activities against Physalospora piricola, Rhizoctonia solani, Sclerotinia sclerotiorum, and Botrytis cinerea. In particular, compound 5c, with 95.5% inhibition rate at a concentration of 50 μg/mL against Physalospora piricola, exhibited a broad spectrum of fungicidal activity. The initial structure-activity relationship indicated that the type of N-substituent on the pyrazole ring would influence the activity and methyl or tert-butyl were more beneficial. The compound 5 with a single benzene ring showed better activity than compound 5 with a bicyclic structure. Besides, compounds with a benzene ring substituent R2 less than four carbons were favorable to enhance fungicidal activity.

Key words: Pyrazole-4-carboxamide, Pyrazole, Tetra-substituted benzene, Fungicidal activity

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