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Structural correlation and computational quantum chemical explorations of two 1,2,3-triazolyl-methoxypyridine derivatives as CYP51 antifungal inhibitors

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Abstract

Structural correlation and computational quantum chemical optimization of two 1,2,3-triazolyl-methoxypyridine derivatives fused with a five-membered heterocyclic moiety, furan (I) or thiophene (II), were performed. Compounds I and II belong to the triclinic crystal classification with P-1 space group. The bond lengths and angles of the optimized crystal structures are in good agreement with the XRD experimental data. We confirmed the hydrogen bonding interactions that observed in crystal packing of compounds I and II using Hirshfeld surface and energy framework analysis. The DFT functional non-linear optical and thermochemistry parameters of the title compounds were calculated. The local reactivity domains of compounds I and II were recognized by the Fukui function parameter analysis. In silico molecular docking simulations were carried out to discover the lanosterol 14 α-demethylase (CYP51) enzyme inhibition against target protein (PDB ID: 1EA1). Antifungal activity of the title molecules was predicted by in vitro antifungal studies against three fungal strains using fungal drug fluconazole as a positive control. Compound I exhibited enhanced affinity with receptor 1EA1 and higher inhibition activity with fungal strains compared to compound II.

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  1. Department of Physics, Thanthai Periyar EVR Government Polytechnic College, Vellore, Tamil Nadu, India

    C. Ravikumar

  2. Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore, Tamil Nadu, India

    S. Murugavel

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Ravikumar, C., Murugavel, S. Structural correlation and computational quantum chemical explorations of two 1,2,3-triazolyl-methoxypyridine derivatives as CYP51 antifungal inhibitors. Struct Chem 30, 2225–2243 (2019). https://doi.org/10.1007/s11224-019-01329-6

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