Hydroxycoumarins as selective MAO-B inhibitors

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Serra, S (Author) Other; Ferino, G (Author) Other; Matos, MJ (Author) Other; Vázquez Rodríguez, S (Author) Other; Delogu, G (Author) Other; Viña, D (Author) Other; Cadoni, E (Author) Other; Santana, L (Author) Other; Uriarte, E (Author) Other

Journal

Title: Bioorganic and Medicinal Chemistry Letters

Vol. 22

Pages: 258-261

ISSN: 0960-894X

Publisher: Elsevier

Indexing

Scopus - 43 Citations

Other information

Authenticus ID: P-00R-0MM

DOI: 10.1016/j.bmcl.2011.11.020

Abstract (EN): A series of 3-aryl-4-hydroxycoumarin derivatives was synthesized with the aim to find out the structural features for the MAO inhibitory activity and selectivity. Methoxy and/or chloro substituents were introduced in the 3-phenyl ring, whereas the position 6 in the coumarin moiety was not substituted or substituted with a methyl group or a chloro atom due to their different electronic, steric and/or lipophilic properties. Most of the synthesized compounds presented MAO-B inhibitory activity. The presence of methoxy and chloro groups, respectively in the para and meta positions of the 3-phenyl ring, have an important influence on the inhibitory activity. Moreover, the presence of a chloro atom in the six position of the moiety (compound 7) improved the inhibitor activity as well as its selectivity against MAO-B compared with iproniazide, used as reference compound. Docking experiments were carried out to understand which are the most energetically preferred orientations adopted by compounds 5, 6 and 7 inside the MAO-B binding pocket.

Language: English

Type (Professor's evaluation): Scientific