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Synthesis of some new 2-(substituted-phenyl)imidazo[4,5-c] and [4,5-b]pyridine derivatives and their antimicrobial activities

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Abstract

The synthesis of 5H-imidazo[4,5-c]pyridines analogues (1a − 1h) and 4H-imidazo[4,5-b]pyridines (3a − 3c) was achieved by reacting 3,4-diaminopyridine or 2,3-diaminopyridine with Na2S2O5 adduct of corresponding benzaldehydes (a1 - a8). Alkylation of compounds (1a − 1h) and (3a − 3c) using 4-chlorobenzyl and /or butyl bromide under basic conditions (K2CO3, DMF) predominantly resulted in the formation of N5 regioisomers (2a − 2l) and N4,3 regioisomers (4a − 4c1,2), respectively. The N5,4,3-regioisomeric structures were confirmed using 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) and HMBC (Heteronuclear Multiple Bond Correlation) spectra. The antibacterial and antifungal activities of the synthesized compounds (2a − 2g, 4a − 5d) were evaluated in vitro against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Methicillin resistant S. aureus, Enterococcus faecalis and Candida albicans, Candida parapsilosis. Among the synthesized compounds, promising activities were observed with compounds 2g, 2h, 4a and 4b with lowest MIC values (4–8 µg/mL). The compounds 2i, 2j, 2k, 2l showed moderate activity. Additionally, a computational approach (ADMETlab 2.0) was used to evaluate the drug likeness properties of the compounds.

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Acknowledgements

Central Laboratory of Pharmacy, Faculty of Ankara University provided support for acquisition of the NMR, mass spectrometer and elemental analyzer used in this work.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, Ankara, Turkey

    Moftah Altaib, Fatima Doganc & Hakan Göker

  2. Department of Microbiology, Faculty of Pharmacy, Ankara University, Ankara, Turkey

    Banu Kaşkatepe

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  1. Moftah Altaib
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  2. Fatima Doganc
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  4. Hakan Göker
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Correspondence to Hakan Göker.

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Altaib, M., Doganc, F., Kaşkatepe, B. et al. Synthesis of some new 2-(substituted-phenyl)imidazo[4,5-c] and [4,5-b]pyridine derivatives and their antimicrobial activities. Mol Divers (2023). https://doi.org/10.1007/s11030-023-10715-6

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