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Artículo

A new insight into non-covalent interactions in 1,4-disubstituted 1H-1,2,3-triazole: synthesis, X-ray structure, DFT calculations, in vitro lipoxygenase Inhibition (LOX) and in silico studies

Ahmed, Muhammad Naeem; Shabbir, Sadia; Batool, Bakhtawar; Mahmood, Tariq; Rashid, Umer; Yasin, Khawaja Ansar; Tahir, Muhammad Nawaz; Arias Cassará, María LucreciaIcon ; Gil, Diego MauricioIcon
Fecha de publicación: 07/2021
Editorial: Elsevier Science
Revista: Journal of Molecular Structure
ISSN: 0022-2860
e-ISSN: 1872-8014
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

Present work deals with the synthesis, characterization, structural properties and in silico studies of ethyl 6-(4-(cyclohexylmethyl)-1H-1,2,3-triazol-1-yl)pyridine-3-carboxylate (1). The synthesized derivative was characterized by spectroscopic as well as single crystal XRD technique. The structure reveals weak non-covalent contacts such as C-H···π, lone pair···π and π···π stacking interactions along with C-H···O and C-H···N hydrogen bonds to form the supramolecular assembly. A detailed analysis of the intermolecular interactions was performed by using the Hirshfeld surface analysis and energy framework calculations, indicating that the dispersion energy is dominant over the electrostatic one in all the structural dimer studied. In addition, the intermolecular interactions have been characterized using the quantum theory of “atoms in molecules”, molecular electrostatic potential (MEP) and the non-covalent interaction plot (NCI plot) index analysis. Compound displayed the IC50 value of IC50 = 37.40 μM in comparison to reference drug indomethacin (IC50 = 48.25 μM) against lipoxygenase (LOX). Docking studies revealed important interactions and binding energy of the compound in comparison with the standard drugs used.
Palabras clave: DFT , DOCKING , LOX , NON-COVALENT INTERACTIONS , TRIAZOLE
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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/148158
DOI: https://doi.org/10.1016/j.molstruc.2021.130283
URL: https://www.sciencedirect.com/science/article/abs/pii/S0022286021004142
Colecciones
Articulos(INBIOFAL)
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Citación
Ahmed, Muhammad Naeem; Shabbir, Sadia; Batool, Bakhtawar; Mahmood, Tariq; Rashid, Umer; et al.; A new insight into non-covalent interactions in 1,4-disubstituted 1H-1,2,3-triazole: synthesis, X-ray structure, DFT calculations, in vitro lipoxygenase Inhibition (LOX) and in silico studies; Elsevier Science; Journal of Molecular Structure; 1236; 7-2021; 1-11
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