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Discovery of potential antifungal triazoles: Design, synthesis, biological evaluation, and preliminary antifungal mechanism exploration

Abstract

A series of triazoles as miconazole analogues were designed, synthesized and characterized by IR, NMR, MS and HRMS spectra. All the newly prepared compounds were screened for their antifungal activities against five fungi. The bioactive assay showed that most of the synthesized compounds exhibited good or even stronger antifungal activities in comparison with reference drugs miconazole and fluconazole. Especially, 3,4-dichlorobenzyl derivative 5b showed comparable or superior activity against all the tested fungal strains to standard drugs, and formed supramolecular complex with CYP51 via the hydrogen bond between the 4-nitrogen of triazole nucleus and histidine residue. Preliminary experiments revealed that both of the active molecules 5b and 9c could intercalate into calf thymus DNA, which might block DNA replication to exert their powerful antifungal abilities. The further study indicated that compound 5b might be stored and transported by human serum albumin through hydrophobic interactions, specific electrostatic interactions and hydrogen bonds. These results strongly suggested that compound 5b could be served as a promising antifungal candidate.

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Publication details

The article was received on 03 Mar 2017, accepted on 09 Jun 2017 and first published on 15 Jun 2017


Article type: Research Article
DOI: 10.1039/C7MD00112F
Citation: Med. Chem. Commun., 2017, Accepted Manuscript
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    Discovery of potential antifungal triazoles: Design, synthesis, biological evaluation, and preliminary antifungal mechanism exploration

    Y. Zhang, G. L. V. Damu, S. Cui, J. Mi, V. K. R. Tangadanchu and C. Zhou, Med. Chem. Commun., 2017, Accepted Manuscript , DOI: 10.1039/C7MD00112F

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