Chinese Journal of Organic Chemistry >
Design, Synthesis, and Biological Evaluation of Novel Sulfonamide 1,2,4-Triazoles and Their Interaction with Calf Thymus DNA
Received date: 2017-08-06
Revised date: 2017-09-02
Online published: 2017-09-19
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
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]. Chinese Journal of Organic Chemistry, 2017 , 37(12) : 3146 -3154 . DOI: 10.6023/cjoc201708010
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