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Synthesis, Characterization, Antimicrobial Activity Screening, and Molecular Docking Study of Pyrimidine Carbonitrile Derivatives

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Abstract

The present work describes the synthesis of 4-amino-6-(2-benzylidenehydrazinyl)-pyrimidine-5-carbonitrile derivatives, 4-amino-6-[(2-phenylethyl)amino]pyrimidine-5-carbonitrile, and 4-amino-6-(piperidin-1-yl)pyrimidine-5-carbonitrile. The compounds were characterized by FT-IR and 1H and 13C NMR spectroscopy and mass spectrometry. All the compounds were evaluated for in vitro antimicrobial activity against different bacterial and fungal strains. The minimum inhibitory concentrations (MICs) of all the compounds were validated. 4-Amino-6-[2-(3,4-dimethoxybenzylidene)hydrazinyl]pyrimidine-5-carbonitrile and 4-amino-6-(piperidin-1-yl)pyrimidine-5-carbonitrile, which have the lowest MIC values were selected for cell leakage analysis and bacterial growth curve study. It was found that both the compounds have potential to induce bacterial cell membrane rupture and disintegration. Field emission scanning electron microscopic analysis confirmed the effect of the selected compounds on the morphology of both Gram-positive (S. aureus) and Gram-negative (E. coli) bacteria. The mechanism of interaction between the drug and the target protein of S. aureus and E. coli was studied by molecular docking.

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ACKNOWLEDGMENTS

The authors are grateful to the Zeiss Microscopy Customer Center, Carl Zeiss India (Bangalore), for providing the FESEM facility.

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  1. Department of Studies in Chemistry, Bangalore University, 560056, Bangalore, India

    Radhika Bhat & Noor Shahina Begum

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  1. Radhika Bhat
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Correspondence to Noor Shahina Begum.

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Bhat, R., Begum, N.S. Synthesis, Characterization, Antimicrobial Activity Screening, and Molecular Docking Study of Pyrimidine Carbonitrile Derivatives. Russ J Org Chem 57, 1352–1360 (2021). https://doi.org/10.1134/S1070428021080169

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