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

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Gomes, LR (Author) Other; Low, JN (Author) Other; Fernando Cagide (Author) FCUP; Chavarria, D (Author) Other; Fernanda Borges (Author) FCUP

Journal

Title: Acta Crystallographica Section E: Crystallographic Communications

Vol. 71

Pages: 547-+

Publisher: International Union of Crystallography

Indexing

ISI Web of Knowledge - 8 Citations

Scopus - 7 Citations

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 37