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Synthesis and Evaluation of Antibacterial Properties of 1,2,3-Triazole Sulfonamide Derivatives

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Abstract

Objective: Currently, microbial infections are a global threat to human health, and there is an urgent need to develop new and effective antibacterial drugs to treat microbial infections. The main purpose of this article is to study the inhibitory effect of sulfonamide compounds containing 1,2,3-triazole rings on bacteria and fungi, in order to seek new antibacterial drugs. Methods: Several sulfonamide compounds with 1,2,3-triazole rings were prepared and their inhibitory effects on seven common human pathogenic bacteria (E. coli, P. aeruginosa, S. typhimurium, S. aureus, and B. subtili, as s well as the fungi C. albicans, and A. niger) were evaluated. And through MOE and Gaussian software, the new molecular docking simulation and molecular quantification calculation of the synthesized compound were carried out to explain the relationship between the antibacterial effect of the compound and its molecular configuration. Results: The results showed that compounds (VIb), (VId), (VIe), (VIf), (VIi), and (VIj) had good antibacterial activity. Among them, (VIe) and (VIf) had similar inhibitory activity against Candida albicans as the positive control drug fluconazole, and (VI) f also had a certain inhibitory effect on Escherichia coli. Discussion: Through antibacterial experiments, we found that the antibacterial effects of (VIe) and (VIf) were the best among the synthesized compounds. Through molecular docking simulation and molecular quantification calculations, we found that compounds (VIe) and (VI) f had a better docking effect with enzymes and the highest molecular energy. They had higher reaction activity and were easy to interact with microbial enzymes, thus exerting antibacterial effects. At the same time, we found that the introduction of amide bonds containing electron donating groups on the benzene ring in triazole sulfonamide significantly enhances the antibacterial activity of the compound. Therefore, we believe that when the electron cloud density on the 1,2,3-triazole ring increases, the antibacterial effect of the compound will be enhanced. Conclusions: 1,2,3-triazole sulfonamides containing amide bonds can serve as potential antibacterial agents.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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ACKNOWLEDGMENTS

The author center thanks Qingdao University of Science and Technology for providing laboratory facilities for this work.

Funding

This work was supported by the National Natural Science Foundation of China (no. 31760521).

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Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science & Technology, Shandong Province, 266000, Qingdao, China

    J. Y. Kong, X. Zhang & G. S. Xuan

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  1. J. Y. Kong
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  2. X. Zhang
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  3. G. S. Xuan
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Contributions

The author KJ mainly participated in the synthesis and biological activity experiments as well as the writing of the paper, while author ZX mainly participated in the separation and purification of products in the synthesis experiments.

Corresponding author

Correspondence to G. S. Xuan.

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Kong, J.Y., Zhang, X. & Xuan, G.S. Synthesis and Evaluation of Antibacterial Properties of 1,2,3-Triazole Sulfonamide Derivatives. Russ J Bioorg Chem 50, 328–344 (2024). https://doi.org/10.1134/S1068162024020122

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  • DOI: https://doi.org/10.1134/S1068162024020122

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