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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2015

Autores

Gomes, LR (Autor) Outra; Low, JN (Autor) Outra; Fernando Cagide (Autor) FCUP; Chavarria, D (Autor) Outra; Fernanda Borges (Autor) FCUP

Revista

Título: Acta Crystallographica Section E: Crystallographic Communications

Vol. 71

Páginas: 547-+

Editora: International Union of Crystallography

Indexação

ISI Web of Knowledge - 8 Citações

Scopus - 7 Citações

Outras Informações

ID Authenticus: P-00H-RM7

DOI: 10.1107/s2056989015007859

Abstract (EN): 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 center dot center dot center dot 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 center dot center dot center dot 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 center dot center dot center dot O intramolecular hydrogen bond constrains the carboxamide moiety such that it is virtually coplanar with the chromone ring.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 37