Synthesis and Biological Activities of Novel Triazolesulfonamide Derivatives Containing Quinolin-2-one Moiety

doi:10.6023/cjoc201510013

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1065-1072.DOI: 10.6023/cjoc201510013 Previous Articles Next Articles

ARTICLE

新型含喹啉酮结构的三唑磺酰胺衍生物的合成及其对线粒体复合物III的抑制活性

程华^a, 汪万强^a, 黄琳^a, 崔萍^a, 吴琼友^b

a. 湖北文理学院化学化工与食品科学学院襄阳 441053;
b. 华中师范大学化学学院农药与生物教育部重点实验室武汉 430079

收稿日期:2015-10-12 修回日期:2015-11-30 发布日期:2016-01-07
通讯作者: 吴琼友 E-mail:qywu@mail.ccnu.edu.cn
基金资助:
国家自然科学基金(No.21272091)、湖北省教育厅项目(No.Q20102606)、中央高校基本科研业务费(No.CCNU15A02014)、襄阳市科技局项目(No.2010GG1B33)、湖北省自然科学基金(No.2014CFC1153)资助项目.

Synthesis and Biological Activities of Novel Triazolesulfonamide Derivatives Containing Quinolin-2-one Moiety

Cheng Hua^a, Wang Wanqiang^a, Huang Lin^a, Cui Ping^a, Wu Qiongyou^b

a. Department of Chemical Engineering, Hubei Universtry of Arts and Science, Xiangyang 441053;
b. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079

Received:2015-10-12 Revised:2015-11-30 Published:2016-01-07
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272091), the Hubei Provincial Department of Education (No. Q20102606), the Fundamental Research Funds for the Central Universities (No. CCNU15A02014), the Xiangyang Science and Technology Bureau (No. 2010GG1B33), and the Natural Science Foundation of Hubei Province (No. 2014CFC1153).

1. Synthesis and Biological Activities of Novel Triazolesulfonamide Derivatives Containing Quinolin-2-one Moiety.PDF(15944KB)

Abstract

Complex III is an essential component for cellular respiration chain and one of the most important targets of fungicides. According to bioisosterism and combination of bioactive sub-structive, a series of novel triazolesulfonamide derivatives containing quinolin-2-one moiety were designed and synthesized. The structures of the synthesized compounds were confirmed by MS, ¹H NMR, ¹³C NMR and elemental analysis. The antibacterial activities of these compounds against porcine complex III were evaluated, and the bioassay results indicated that the target compound 6f [IC₅₀=(45.75±1.02) μmol/L] showed much higher inhibitory potency (more than one-fold higher) against complex III than that of the control amisulbrom [IC₅₀=(92.96±1.30) μmol/L], thus compound 6f may recognize as a lead for further structure modification.

Key words: quinolin-2-one, 1,2,4-triazolesulfonamide, porcine succinate-cyctochrome reductase, biological activity, synthesis

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Cheng Hua, Wang Wanqiang, Huang Lin, Cui Ping, Wu Qiongyou. Synthesis and Biological Activities of Novel Triazolesulfonamide Derivatives Containing Quinolin-2-one Moiety[J]. Chin. J. Org. Chem., 2016, 36(5): 1065-1072.

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新型含喹啉酮结构的三唑磺酰胺衍生物的合成及其对线粒体复合物III的抑制活性

Synthesis and Biological Activities of Novel Triazolesulfonamide Derivatives Containing Quinolin-2-one Moiety

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