Citation: 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 shu

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

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

Corresponding author: Zhang Huizhen, zhanghuizhen@lyu.edu.cn
Received Date: 6 August 2017
Revised Date: 2 September 2017
Available Online: 19 December 2017
Fund Project: the National Natural Science Foundation of China 21672173the Shandong Provincial Natural Science Foundation ZR2016CP22the Doctoral Scientific Research Foundation of Linyi University LYDX2016BS030Project 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 Studentsthe Shandong Provincial Natural Science Foundation ZR2017PB001

Figures(8)

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.
- sulfonamide,
- 1, 2, 4-triazole,
- synthesis,
- antimicrobial,
- calf thymus DNA
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