Browsing by Author "Chavarria, Daniel"
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- New insights in the discovery of novelh-MAO-B inhibitors: structural characterization of a series ofN-phenyl-4-oxo-4H-chromene-3-carboxamide derivativesPublication . Gomes, Ligia R.; Low, John Nicolson; Cagide, Fernando; Chavarria, Daniel; Borges, FernandaSix 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.