New insights in the discovery of novel h-MAO-B inhibitors: structural characterization of a series of N-phenyl-4-oxo-4H-chromene-3-carboxamide derivatives

oleh: Ligia R. Gomes, John Nicolson Low, Fernando Cagide, Daniel Chavarria, Fernanda Borges

Format: Article
Diterbitkan: International Union of Crystallography 2015-05-01

Deskripsi

Six N-substituted-phenyl 4-oxo-4H-chromene-3-carboxamides, namely N-(2-nitrophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10N2O5 (2b), N-(3-methoxyphenyl)-4-oxo-4H-chromene-3-carboxamide, C17H13NO4, (3a), N-(3-bromophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10BrNO3, (3b), N-(4-methoxyphenyl)-4-oxo-4H-chromene-3-carboxamide, C17H13NO4, (4a), N-(4-methylphenyl)-4-oxo-4H-chromene-3-carboxamide, C17H13NO3, (4d), and N-(4-hydroxyphenyl)-4-oxo-4H-chromene-3-carboxamide, C16H11NO4, (4e), have been structurally characterized. All compounds exhibit an anti conformation with respect to the C—N rotamer of the amide and a trans-related conformation with the carbonyl groups of the chromone ring of the amide. These structures present an intramolecular hydrogen-bonded network comprising an N—H...O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak Car—H...O hydrogen bond in which the carbonyl group of the amide acts as acceptor for the H atom of an ortho-C atom of the exocyclic phenyl ring, which results in another S(6) ring. The N—H...O intramolecular hydrogen bond constrains the carboxamide moiety such that it is virtually coplanar with the chromone ring.