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In Silico Docking Studies, Synthesis, Characterization, and Antimicrobial Antimycobacterial Activity of Coumarinyl Oxadiazoles from Fatty Acids

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Abstract

This present study deals with the design and evaluation of novel coumarinyl oxadiazoles substituted fatty acids derivatives using synthetic approach and to screen for in vitro antimicrobial activity. A recent literature survey revealed that, coumarinyl oxadiazoles substituted fatty acids derivatives shown for their ability to improve biological activities The condensation of 2-oxo-2H-chromene-3-carbohydrazide with substituted fatty acids in the presence of phosphorus oxychloride yielded a variety of novel 5-N-alkyl-1,3,4-oxadiazole-2H-chromen-2-one derivatives. The structure of the newly synthesized compounds was validated by elemental analysis, IR, 1H NMR, and mass spectrum data. Further, analysis of the drug-likeness property is predicted through five parameters like Lipinski rule, Ghose, Egan, Vebers, and Muegge rules. As molcular docking is normally used for understanding drug-receptor interaction. The above-derived compounds were subjected to molcular docking studies (4MFI, 5E2C, 6FBV, and 6NNE). The antibacterial and anti-mycobacterial properties of these substances were investigated. Compounds 3-(5-dodecyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one and 3-(5-hexadecyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one demonstrated considerable antibacterial activity against several tested bacterial strains in antimicrobial tests. In comparison to standard, compound 3-(5-(heptadec-8-en-1-yl)-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one demonstrated excellent antitubercular action. This hypothesis provides a possible explanation of the enhanced biological activity of the derived compounds.

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ACKNOWLEDGMENTS

The authors are appreciative to Creative Educational Society’s College of Pharmacy in Kurnool, Andhra Pradesh, India, for providing laboratory facilities in a timely manner, allowing them to successfully complete this research project. The authors would like to express their gratitude to SRM University in Chennai, Tamil Nadu, for their assistance in recording the 1H NMR and mass spectra.

Funding

This work was supported by regular institutional funding, and no additional grants were obtained.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Santhiram College of Pharmacy, JNTU, Anantapur, Nandyal, 518112, Andhra Pradesh, India

    B. Naga Sudha & N. Yella Subbaiah

  2. Department of Pharmaceutical Chemistry, SRM College of Pharmacy, SRM Institute of Science and Technology, Kattankulathur, Chengalpattu (Dt), 603203, Tamil Nadu, India

    B. Siva Kumar

  3. Department of Pharmaceutical Quality Assurance, SRM College of Pharmacy, SRM Institute of Science and Technology, Kattankulathur, Chengalpattu (Dt), 603203, Tamil Nadu, India

    K. Ilango

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  1. B. Naga Sudha
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Contributions

Authors BNS, NYS, and BSK designed the experiments. Authors BNS and BSK synthesized the samples and carried out their electrochemical study. Authors BSK and KI carried out studies using Raman and NMR spectroscopy. Authors BNS, KI participated in data processing. Authors BNS, NYS, BSK, and KI made theoretical calculations. Authors BNS, NYS, BSK, and KI contributed to manuscript preparation. All authors participated in the discussions.

Corresponding author

Correspondence to B. Naga Sudha.

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The data that support the findings of this study are available from the corresponding author upon reasonable request. This article does not contain any studies involving animals or human participants performed by any of the authors. Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Sudha, B.N., Subbaiah, N.Y., Kumar, B.S. et al. In Silico Docking Studies, Synthesis, Characterization, and Antimicrobial Antimycobacterial Activity of Coumarinyl Oxadiazoles from Fatty Acids. Russ J Bioorg Chem 49, 1389–1397 (2023). https://doi.org/10.1134/S1068162023060195

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