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Solvent-free synthesis and antibacterial evaluation of novel mercaptobenzenesulfonamides

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Abstract

In this research, a set of novel mercaptobenzenesulfonamides were synthesized and evaluated as potential antibacterial agents. These novel sulfonamides were synthesized in three steps, including acylation of 2-aminothiophenol, chlorosulfonation of the obtained 2-mercaptophenyl acetamide, and finally the reaction of aromatic amines with 4-acetamide-3-mercaptobenzene-1-sulfonyl chloride. The chemical structure of the prepared sulfonamides was verified by IR, 1H-NMR, and 13C-NMR spectroscopy. The antibacterial activity of the synthesized compounds was also analyzed by the agar diffusion method against Staphylococcus aureus and Escherichia coli bacteria. Furthermore, computational ducking calculation and Pharmacophoric studies of sulfonamides were conducted by AutoDock Vina software and ZINCPharmer methods, respectively. According to the in vitro antibacterial evaluation as well as the computational results, mercaptobenzenesulfonamides with methoxy, hydroxy, and chloro substituents showed the highest antibacterial activity compared to other synthesized sulfonamides.

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Authors and Affiliations

  1. Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza, Isfahan, 86145-311, Iran

    Elham Ghased, Hamid Ardeshiri Lordejani, Mojtaba Vedaei & Ahmad Reza Massah

  2. Razi Chemistry Research Center, Islamic Azad University, Shahreza Branch, Shahreza, Isfahan, 86145-311, Islamic Republic of Iran

    Mojtaba Vedaei & Ahmad Reza Massah

Authors
  1. Elham Ghased
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  2. Hamid Ardeshiri Lordejani
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Correspondence to Ahmad Reza Massah.

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Ghased, E., Lordejani, H.A., Vedaei, M. et al. Solvent-free synthesis and antibacterial evaluation of novel mercaptobenzenesulfonamides. J IRAN CHEM SOC 20, 911–919 (2023). https://doi.org/10.1007/s13738-022-02712-7

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