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

Borges, F.²  Gomes, L.R.³  Chavarria, D.⁴  Cagide, F.⁵  Low, J.N.⁸ 

[1]CIQ/Departamento de Quι

[2]Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland

[3]FP-ENAS-Faculdade de Ciê

[4]de da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal

[5]de, Escola Superior de Saú

[6]mica e Bioquι

[7]mica, Faculdade de Ciê

[8]ncias de Saú

[9]ncias, Universidade do Porto, 4169-007 Porto, Portugal

关键词: CRYSTAL STRUCTURE;    DRUG DESIGN;    CHROMONES;    CONFORMATION;    SUPRAMOLECULAR STRUCTURE;    HYDROGEN BONDING;   

DOI  :  10.1107/S2056989015007859

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

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.

【 授权许可】

CC BY