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Publication
New insights in the discovery of novelh-MAO-B inhibitors: structural characterization of a series ofN-phenyl-4-oxo-4H-chromene-3-carboxamide derivatives
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Advisor(s)
Abstract(s)
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.
Description
Keywords
Crystal structure Drug design Chromones Conformation Supramolecular structure Hydrogen bonding
Citation
Gomes, L. R., Low, J. N., Cagide, F., Chavarria, D., & Borges, F. (2015). 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. Acta crystallographica. Section E, Crystallographic communications, 71(Pt 5), 547–554. doi:10.1107/S2056989015007859
Publisher
International Union of Crystallography