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Synthesis of novel indole-oxindole clubbed 1,2,3-triazole hybrids: antimicrobial evaluation and molecular docking study

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Abstract

A new series of indole-oxindole clubbed 1,2,3-triazole hybrids 5(a–o) was thoughtfully designed and synthesized via Cu-catalysed azide-alkyne cycloaddition (CuAAC) click reaction while taking into account the varied medicinal activities of indole, oxindole, and 1,2,3-triazole derivatives. By employing the broth micro dilution method, the antimicrobial potential of each synthesized hybrid molecule was examined against three gram-negative (Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia), three gram-positive (Bacillus subtilis, Staphylococcus aureus, and Streptococcus pyogenes), and two fungal strains (Candida albicans and Aspergillus niger). Compound 5e was shown to be the best antibacterial agent with a minimum inhibitory concentration (MIC) of 25 μg/mL against Escherichia coli among all the synthetics. Molecular docking study also streamlined the plausible interactions of compound 5e with the active site of DNA gyrase. The SwissADME webserver analysis revealed that the majority of synthetic compounds adhere to the principles of drug-likeness.

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Acknowledgements

This research was supported by the Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Gujarat, India. All the authors are grateful to UGC-CAS, Phase-II sponsored under award latter no. F-540/5/CASII/2018 (SAP-I) dated 25 July, 2018 for the assistance in general. Jaydeep A. Mokariya is grateful to CSIR for CSIR SRF fellowship (CSIR Award No: 09/157(0056)/2018-EMR-I). One of the authors (Reenaben C. Patel) is grateful to the SHODH-ScHeme Of Developing High quality research, student Ref No: 202001640027, Education Department, Gujarat State.

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  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388120, Gujarat, India

    Jaydeep A. Mokariya, Reena C. Patel & Manish P. Patel

  2. Microcare Laboratory & TRC, 105, Manthan Point, Una Pani Rd, Lal Darwaja, Haripura, Surat, 395003, Gujarat, India

    Dhanji P. Rajani

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  1. Jaydeep A. Mokariya
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Contributions

J.A.M. contributed to the conceptualization of this work and carried out the synthesis design and computational study and writing—reviewing & editing the manuscript. R.C.P. contributed to the synthesis experimental study and wrote the original draft of the manuscript. D.P.R. contributed to biological activity. M.P.P. conceptualized and supervised this work. All the authors reviewed the manuscript.

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Correspondence to Manish P. Patel.

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Mokariya, J.A., Patel, R.C., Rajani, D.P. et al. Synthesis of novel indole-oxindole clubbed 1,2,3-triazole hybrids: antimicrobial evaluation and molecular docking study. Res Chem Intermed 49, 2933–2953 (2023). https://doi.org/10.1007/s11164-023-05024-4

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