RT Journal Article
T1 MAO inhibitory activity of bromo-2- phenylbenzofurans: synthesis, in vitro study, and docking calculations
A1 Delogu, Giovanna Lucia
A1 Mayán, Lucía
A1 Matos, Maria João
A1 Vilar Varela, Santiago
A1 Hripcsak, George
A1 Borges, Fernanda
A1 Viña Castelao, María Dolores
A1 Pintus, Francesca
A1 Munín, J.
A1 Fontenla Gil, José Ángel
K1 MAO inhibitors
K1 Phenylbenzofurans
K1 In vitro study
K1 Docking calculations
AB Monoamine oxidase (MAO) is an enzyme responsible for metabolism of monoamine neurotransmitters which play an important role in brain development and function. This enzyme exists in two isoforms, and it has been demonstrated that MAO-B activity, but not MAO-A activity, increases with aging. MAO inhibitors show clinical value because besides the monoamine level regulation they reduce the formation of byproducts of the MAO catalytic cycle, which are toxic to the brain. A series of 2-phenylbenzofuran derivatives was designed, synthesized and evaluated against hMAO-A and hMAO-B enzymes. A bromine substituentwas introduced in the 2-phenyl ring, whereas position 5 or 7 of the benzofuran moiety was substituted with a methyl group. Most of the tested compounds inhibited preferentially MAO-B in a reversible manner, with IC50 values in the low micro or nanomolar range. The 2-(2′-bromophenyl)-5-methylbenzofuran (5) was the most active compound identified (IC50 = 0.20 μM). In addition, none of the studied compounds showed cytotoxic activity against the human neuroblastoma cell line SH-SY5Y. Molecular docking simulations were used to explain the observed hMAO-B structure–activity relationship for this type of compounds.
PB Royal Society of Chemistry
SN 2040-2503
YR 2017
FD 2017-07-05
LK http://hdl.handle.net/10347/32079
UL http://hdl.handle.net/10347/32079
LA eng
NO Delogu, G.L., Pintus, F., Mayán, L., Matos, M.J., Vilar, S., Munín, J., Fontenla, J.A., Hripcsak, G., Borges, F., Viña, D. (2017), MAO inhibitory activity of bromo-2- phenylbenzofurans: synthesis, in vitro study, and docking calculations, "Med. Chem. Commun.", 8, 1788
NO Financial support from the Consellería de Cultura, Educación e Ordenación Universitaria (EM2014/016 and the Centro Singular de Investigación de Galicia Accreditación 2016–2019, ED431G/05) and the European Regional Development Fund (ERDF) is gratefully acknowledged. Financial support from the Fondazione Banco di Sardegna – Università degli Studi di Cagliari – Progetti di Ricerca di Interesse Dipartimentale (PRID) is also acknowledged. The authors would like to thank “Angeles Alvariño, Plan Galego de Investigación, Innovación e Crecemento 2011–2015 (I2C)”, and the European Social Fund (ESF). G. L. Delogu is grateful to R. Mascia (University of Cagliari)for his technical assistance.
DS Minerva
RD 22 abr 2026