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

Gomes, Ligia R.; Low, John Nicolson; Cagide, Fernando; Gaspar, Alexandra; Borges, Fernanda

http://hdl.handle.net/10284/8169

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Abstract(s)

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)°]. 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)° in (3) and (4), respectively. Compound (3) shows a short C-H...O intramolecular contact forming an S(7) ring. The supramolecular structures for each compound are defined by weak C-H...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.

Keywords

Crystal structure Chromones; Pharmalogical activity Supramolecular structure Hydrogen bonding

URI

http://hdl.handle.net/10284/8169

Citation

Gomes, L. R., Low, J. N., Cagide, F., Gaspar, A., & Borges, F. (2015). 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. Acta crystallographica. Section E, Crystallographic communications, 71(Pt 11), 1270–1277. doi:10.1107/S2056989015017958