新型取代苯甲酰胺类化合物的合成及对 AHAS酶的抑制和除草活性

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (8): 1574.

新型取代苯甲酰胺类化合物的合成及对 AHAS酶的抑制和除草活性

李文明, 王建国, 李永红, 王素华, 李正名

南开大学元素有机化学国家重点实验室, 南开大学农药国家工程研究中心, 天津 300071

收稿日期:2009-11-06 出版日期:2010-08-10 发布日期:2010-08-10
通讯作者: 李正名.E-mail: nkzml@vip.163.com; 王建国. E-mail: nkwjg@nankai.edu.cn
基金资助:
国家“九七三”计划项目(批准号: 2010CB126103)和国家自然科学青年基金(批准号: 20602021)资助.

Synthesis of Some Novel Substituted Benzamides, Their Inhibition of AHAS and Herbicidal Activity

LI Wen-Ming, WANG Jian-Guo*, LI Yong-Hong, WANG Su-Hua, LI Zheng-Ming*

State Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center, Nankai University, Tianjin 300071, China

Received:2009-11-06 Online:2010-08-10 Published:2010-08-10
Contact: LI Zheng-Ming.E-mail: nkzml@vip.163.com; WANG Jian-Guo. E-mail: nkwjg@nankai.edu.cn
Supported by:
国家“九七三”计划项目(批准号: 2010CB126103)和国家自然科学青年基金(批准号: 20602021)资助.

摘要/Abstract

摘要： 在对乙酰乳酸合成酶(AHAS)抑制剂进行生物合理设计的基础上, 分别以4-氟-3硝基苯胺和2-胺基-5硝基苯腈为原料, 合成了8个苯磺酰胺基苯甲酰胺类化合物和7个双苯磺酰胺基苯甲酰胺类化合物, 其结构通过核磁共振谱、质谱、红外光谱及元素分析验证. 初步的生物活性测定结果表明，部分化合物在体内和体外均具有一定的生物活性, 其中化合物4c, 4d和7c在100 μg/mL浓度下对拟南芥AHAS的抑制率分别为66%, 76% 和68%, 而化合物4a, 4c, 7a和7b在100 μg/mL浓度下对油菜根长的抑制率分别为76%, 70%, 89% 和82%. 研究结果为进一步设计合成潜在的AHAS抑制剂提供了有益参考.

关键词: 苯甲酰胺, AHAS抑制剂, 除草活性

Abstract: Based on the strategy of bio-rational design of AHAS inhibitors, 8 novel N-(phenylsulfonamidophenyl)benzamide and 7 novel N-{[N-(phenylsulfonyl)phenylsulfonamido] phenyl}benzamide derivatives were designed and synthesized by starting materials 4-fluoro-3-nitroaniline and 2-amino-5-nitrobenzonitrile, and their structures were confirmed by IR, MS, ¹H NMR and elemental analysis. The preliminary bioassay indicated that some compounds exhibited bioactivity either in vitro or in vivo. Compounds 4c, 4d and 7c show inhibition to Arabidopsis thaliana AHAS of 66%, 76% and 68% at 100 μg/mL. Compound 4a, 4c, 7a and 7b show inhibition on the growth of rape root of 76%, 70%, 89% and 82% at 100 μg/mL. The present results provide helpful guidance to further design more potential AHAS inhibitors.

Key words: Benzamide, AHAS inhibitor, Herbicidal activity

TrendMD:

李文明, 王建国, 李永红, 王素华, 李正名. 新型取代苯甲酰胺类化合物的合成及对 AHAS酶的抑制和除草活性. 高等学校化学学报, 2010, 31(8): 1574.

LI Wen-Ming, WANG Jian-Guo*, LI Yong-Hong, WANG Su-Hua, LI Zheng-Ming*. Synthesis of Some Novel Substituted Benzamides, Their Inhibition of AHAS and Herbicidal Activity. Chem. J. Chinese Universities, 2010, 31(8): 1574.

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