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Synthesis and Antimicrobial, Antioxidant, ADME-T, and Molecular Docking Studies of Imidazo[1,2-a]pyridine Derivatives

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Abstract

A novel series of imidazopyridine Schiff bases have been synthesized by the acid-catalyzed reaction of 7-methyl-2-phenylimidazo[1,2-a]pyridin-3-amine with different aromatic aldehydes. The newly synthesized compounds were characterized by 1H and 13C NMR spectra and LC/MS data and screened for their antibacterial and antifungal activities against two bacterial strains (Pseudomonas aeruginosa and Escherichia coli) and one pathogenic fungal strain (Fusarium oxysporum f. sp. Albedinis) using disk diffusion method. Also, their antioxidant activity was evaluated using DPPH free radical scavenging method. Preliminary bioassay results showed that one of the synthesized compounds showed significant activity against the tested bacterial and fungal strains, while all the compounds displayed moderate antioxidant activities. The structure–activity relationship study revealed that the activity strongly depends on the substitution pattern. On the other hand, in silico ADME-Tox predictions and molecular docking studies were carried out to determine the bioavailability of the synthesized compounds and confirm the antifungal and antibacterial experimental findings.

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ACKNOWLEDGMENTS

This work was supported by Mohammed I University. The authors thank the staff of “Laboratoire de Chimie, équipe Matériaux Fonctionnels & Photoniques UMR 5182/CNRS-ENS Lyon-Université (Lyon 1, France)” for recording the 1H and 13C NMR spectra.

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Authors and Affiliations

  1. Laboratory of Molecular Chemistry, Materials, and Environment, Polydisciplinary Faculty of Nador, Mohammed First University, 60000, Oujda, Morocco

    M. Koudad, A. El Aatiaoui, M. Azzouzi & A. Oussaid

  2. Laboratory of Applied Chemistry and Environment (LCAE), Department of Chemistry, Faculty of Sciences, Mohammed First University, 60000, Oujda, Morocco

    S. Dadou, F. Abrigach & N. Benchat

  3. Institute of Nursing Professions and Health Techniques Fez, El Ghassani Hospital, 30000, Fez, Morocco

    M. Allali

  4. Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco

    K. Karrouchi

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  1. M. Koudad
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  2. S. Dadou
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  4. A. El Aatiaoui
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Correspondence to K. Karrouchi.

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Koudad, M., Dadou, S., Abrigach, F. et al. Synthesis and Antimicrobial, Antioxidant, ADME-T, and Molecular Docking Studies of Imidazo[1,2-a]pyridine Derivatives. Russ J Org Chem 59, 1237–1247 (2023). https://doi.org/10.1134/S1070428023070163

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