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
Moreno-Fuquen, Rodolfo and Hurtado-Angulo, Mario and Arango-Daravina, Kevin and Bain, Gavin and Kennedy, Alan R. (2020) 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. Acta Crystallographica Section E: Structure Reports, E76 (11). pp. 1762-1767. ISSN 1600-5368 (https://doi.org/10.1107/S2056989020013730)
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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 - H⋯O and C - H⋯O hydrogen bonds, forming fused R 22(18), R 34(30), R 44(38) rings running along [ 0 ] and R 33(37) and R 33(15) rings along [001]. Hirshfeld analysis was undertaken to study the intermolecular 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 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 mol-1 from the value for the molecule Apixaban, which was used as a positive control inhibitor. This suggests the title compound exhibits inhibitory activity.
ORCID iDs
Moreno-Fuquen, Rodolfo, Hurtado-Angulo, Mario, Arango-Daravina, Kevin, Bain, Gavin and Kennedy, Alan R. ORCID: https://orcid.org/0000-0003-3652-6015;-
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Item type: Article ID code: 74349 Dates: DateEvent30 November 2020Published13 October 2020AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 23 Oct 2020 15:03 Last modified: 03 Dec 2024 01:21 URI: https://strathprints.strath.ac.uk/id/eprint/74349