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.

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 R 2 2(18), R 3 4(30), R 4 4(38) rings running along [0] and R 3 3(37) and R 3 3(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.

SUBMITTER: Moreno-Fuquen R 

PROVIDER: S-EPMC7643242 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature