Design, Synthesis, and Biological Evaluation of Novel Sulfonamide 1,2,4-Triazoles and Their Interaction with Calf Thymus DNA

doi:10.6023/cjoc201708010

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3146-3154.DOI: 10.6023/cjoc201708010 Previous Articles Next Articles

Articles

新型磺胺1,2,4-三唑类化合物的设计合成、抗微生物活性及与小牛胸腺DNA相互作用研究

刘庆龙^a, 房鹏金^a, 赵志龙^a, 张慧珍^a, 周成合^b

a 临沂大学药学院临沂 276000;
b 西南大学化学化工学院重庆 400715

收稿日期:2017-08-06 修回日期:2017-09-02 发布日期:2017-09-19
通讯作者: 张慧珍 E-mail:zhanghuizhen@lyu.edu.cn
基金资助:
国家自然科学基金（No.21672173）、山东省自然科学基金（No.ZR2017PB001，ZR2016CP22）、临沂大学博士启动基金（No.LYDX2016BS030）和国家级大学生创新创业训练计划资助项目.

Design, Synthesis, and Biological Evaluation of Novel Sulfonamide 1,2,4-Triazoles and Their Interaction with Calf Thymus DNA

Liu Qinglong^a, Fang Pengjin^a, Zhao Zhilong^a, Zhang Huizhen^a, Zhou Chenghe^b

a School of Pharmacy, Linyi University, Linyi 276000;
b School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715

Received:2017-08-06 Revised:2017-09-02 Published:2017-09-19
Contact: 10.6023/cjoc201708010 E-mail:zhanghuizhen@lyu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21672173), the Shandong Provincial Natural Science Foundation (No. ZR2017PB001, ZR2016CP22), the Doctoral Scientific Research Foundation of Linyi University (No. LYDX2016BS030) and the National Innovative Training Program for College Students.

1. Design, Synthesis, and Biological Evaluation of Novel Sulfonamide 1,2,4-Triazoles and Their Interaction with Calf Thymus DNA.PDF(376KB)

Abstract

Sulfonamides as an important type of chemotherapeutic drugs have been one of the research topics recently. A series of sulfonamide 1,2,4-triazoles were successfully synthesized starting from commercial acetanilide via a multi-step sequence of sulfonylation, aminolysis and N-alkylation, and were confirmed by IR, ¹H NMR, ¹³C NMR, MS as well as HRMS spectra. All the synthesized new compounds were evaluated for their in vitro antibacterial and antifungal activities. The bioactive assay showed that most of the synthesized compounds exhibited better inhibitory potency than sulfanilamide against all tested bacterial strains, and most of the compounds gave good anti-Escherichia coli activity in comparison with other microorganisms. Especially, N-(4-(N-(2-(1H-1,2,4-triazol-1-yl)ethyl)-N-(3-fluorobenzyl)sulfamoyl)phenyl) acetamide (7b) bearing m-fluorobenzyl group exhibited excellent antibacterial activities against Escherichia coli with minimal inhibition concentration (MIC) value of 16 mg/mL. Preliminary research revealed that compound 7b could effectively intercalate into calf thymus DNA to form compound 7b-DNA complex which might block DNA replication and thus exert antimicrobial activities.

Key words: sulfonamide, 1,2,4-triazole, synthesis, antimicrobial, calf thymus DNA

Cite this article

Liu Qinglong, Fang Pengjin, Zhao Zhilong, Zhang Huizhen, Zhou Chenghe. Design, Synthesis, and Biological Evaluation of Novel Sulfonamide 1,2,4-Triazoles and Their Interaction with Calf Thymus DNA[J]. Chin. J. Org. Chem., 2017, 37(12): 3146-3154.

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新型磺胺1,2,4-三唑类化合物的设计合成、抗微生物活性及与小牛胸腺DNA相互作用研究

Design, Synthesis, and Biological Evaluation of Novel Sulfonamide 1,2,4-Triazoles and Their Interaction with Calf Thymus DNA

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