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



刘庆龙a, 房鹏金a, 赵志龙a, 张慧珍a, 周成合b   

  1. 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
  • 基金资助:


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

Liu Qinglonga, Fang Pengjina, Zhao Zhilonga, Zhang Huizhena, Zhou Chengheb   

  1. 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
  • 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.

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