Synthesis, crystal structure, Hirshfeld surface analysis, MEP study and mol-ecular docking of N -{3-[(4-meth-oxy-phen-yl)carbamo-yl]phen-yl}-3-nitro-benzamide as a promising inhibitor of hfXa

Acta Crystallographica. Section E, Crystallographic Communications
Rodolfo Moreno-FuquenAlan R Kennedy

Abstract

The title compound, C21H17N3O5, consists of three rings, A, B and C, linked by amide bonds with the benzene rings A and C being inclined to the mean plane of the central benzene ring B by 2.99 (18) and 4.57 (18)°, respectively. In the crystal, mol-ecules are linked via N-H⋯O and C-H⋯O hydrogen bonds, forming fused R22(18), R34(30), R44(38) rings running along [0] and R33(37) and R33(15) rings along [001]. Hirshfeld analysis was undertaken to study the inter-molecular contacts in the crystal, showing that the most significant contacts are H⋯O/O⋯H (30.5%), H⋯C/C⋯H (28.2%) and H⋯H (29.0%). Two zones with positive (50.98 and 42.92 kcal mol-1) potentials and two zones with negative (-42.22 and -34.63 kcal mol-1) potentials promote the N-H⋯O inter-actions in the crystal. An evaluation of the mol-ecular coupling of the title compound and the protein with enzymatic properties known as human coagulation factor Xa (hfXa) showed the potential for coupling in three arrangements with a similar minimum binding energy, which differs by approximately 3 kcal mol-1 from the value for the mol-ecule Apixaban, which was used as a positive control inhibitor. This suggests the title compound exhibits inhibitory activity.

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Methods Mentioned

BETA
X-ray
acyl­ation

Software Mentioned

Gauss View
Multiwfn
ROTAX
CrystalExplorer
PyMOL
Gauss09W
Autodock Vina
Ligplot +

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