Title of article :
Synthesis, crystal structure, Hirshfeld surface analysis, MEP study and molecular docking of N-{3-[(4-methoxyphenyl)carbamoyl]phenyl}-3-nitrobenzamide as a promising inhibitor of hfXa
Author/Authors :
Moreno-Fuquen, Rodolfo Grupo de Cristalografía - Departamento de Química - Universidad del Valle, Colombia , Hurtado-Angulo, Mario Grupo de Cristalografía - Departamento de Química - Universidad del Valle, Colombia , Arango-Daraviña, Kevin Grupo de Cristalografía - Departamento de Química - Universidad del Valle, Colombia , Bain, Gavin WestCHEM. Department of Pure and Applied Chemistry - University of Strathclyde, Scotland , Kennedy, Alan R. WestCHEM. Department of Pure and Applied Chemistry - University of Strathclyde, Scotland
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, molecules are linked via N—HO and C—HO hydrogen bonds,
forming fused R2 2(18), R3 4(30), R4 4(38) rings running along [101] and R3
3(37) and R3 3(15) rings along [001]. Hirshfeld analysis was undertaken to study the
intermolecular contacts in the crystal, showing that the most significant contacts
are HO/OH (30.5%), HC/CH (28.2%) and HH (29.0%). Two zones with positive (50.98 and 42.92 kcal mol1 ) potentials and two zones wit h negative (42.22 and 34.63 kcal mol1
) potentials promote the N—HO interactions in the crystal. An evaluation of the molecular 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 mol1 from the value for the molecule Apixaban, which
was used as a positive control inhibitor. This suggests the title compound exhibits inhibitory activity.
Keywords :
crystal structure , Hirshfeld surfaces , molecular electrostatic potential , molecular dockin
Journal title :
Acta Crystallographica Section E: Crystallographic Communications