A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B

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

Authors

Gomes, LR (Author) Other; Low, JN (Author) Other; Fernando Cagide (Author) FCUP; Gaspar, A (Author) Other; Fernanda Borges (Author) FCUP

Journal

Title: Acta Crystallographica Section E: Crystallographic Communications

Vol. 71

Pages: 1270-+

Publisher: International Union of Crystallography

Indexing

ISI Web of Knowledge - 2 Citations

Scopus - 3 Citations

Other information

Authenticus ID: P-00K-1K5

DOI: 10.1107/s2056989015017958

Abstract (EN): The crystal structures of the 3-substituted tertiary chromone carboxamide derivative, C17H13NO3, N-methyl-4-oxo-N-phenyl-4H-chromene-3-carboxamide (1), and the chromone carbonyl pyrrolidine derivatives, C14H13NO3, 3-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (3) and 2-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (4) have been determined. Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities. The chromone carboxamide presents a -syn conformation with the aromatic rings twisted with respect to each other [the dihedral angle between the mean planes of the chromone system and the exocyclic phenyl ring is 58.48 (8)degrees]. The pyrrolidine derivatives also display a significant twist: the dihedral angles between the chromone system and the best plane formed by the pyrrolidine atoms are 48.9 (2) and 23.97 (12)degrees in (3) and (4), respectively. Compound (3) shows a short C-H center dot center dot center dot O intramolecular contact forming an S(7) ring. The supramolecular structures for each compound are defined by weak C-H center dot center dot center dot O hydrogen bonds, which link the molecules into chains and sheets. The Cambridge Structural Database gave 45 hits for compounds with a pyrrolidinecarbonyl group. A simple statistical analysis of their geometric parameters is made in order to compare them with those of the molecules determined in the present work.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 20