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Synthesis, characterization, antimicrobial, antioxidant and computational evaluation of N-acyl-morpholine-4-carbothioamides

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Abstract

The present research paper reports the convenient synthesis, successful characterization, in vitro antibacterial, antifungal, antioxidant potency and biocompatibility of N-acyl-morpholine-4-carbothioamides (5a–5j). The biocompatible derivatives were found to be highly active against the tested bacterial and fungal strains. Moreover, some of the screened N-acyl-morpholine-4-carbothioamides exhibited excellent antioxidant potential. Docking simulation provided additional information about possibilities of their inhibitory potential against RNA. It has been predicted by in silico investigation of the binding pattern that compounds 5a and 5j can serve as the potential surrogate for design of novel and potent antibacterial agents. The results for the in vitro bioassays were promising with the identification of compounds 5a and 5j as the lead and selective candidate for RNA inhibition. Results of the docking computations further ascertained the inhibitory potential of compound 5a. Based on the in silico studies, it can be suggested that compounds 5a and 5j can serve as a structural model for the design of antibacterial agents with better inhibitory potential.

Graphic abstract

Binding mode of compound 5j inside the active site of RNA in 3D space. 5j displayed highest antibacterial potential than the reference drug ampicillin with ZOI 10.50 mm against Staphylococcus aureus. 5j also displayed highest antifungal potential than the reference drug amphotericin B with ZOI 18.20 mm against Fusarium solani.

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Acknowledgements

The author Mr. Hamid Aziz is highly grateful to the Higher Education Commission (HEC), Pakistan, for providing indigenous scholarship as the financial support for the research work performed.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-I-Azam University, Islamabad, 45320, Pakistan

    Hamid Aziz & Aamer Saeed

  2. Department of Biotechnology, Quaid-I-Azam University, Islamabad, 45320, Pakistan

    Muhammad Aslam Khan & Shakeeb Afridi

  3. Department of Biology, Laurentian University, 935 Ramsey Lake Road, Sudbury, ON, P3E 2C6, Canada

    Farukh Jabeen

  4. Computation, Science, Research and Development Organization, 1401, 2485 Hurontario Street, Mississauga, ON, L5A2G6, Canada

    Farukh Jabeen

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  1. Hamid Aziz
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Aziz, H., Saeed, A., Khan, M.A. et al. Synthesis, characterization, antimicrobial, antioxidant and computational evaluation of N-acyl-morpholine-4-carbothioamides. Mol Divers 25, 763–776 (2021). https://doi.org/10.1007/s11030-020-10054-w

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