Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

Vilches-Herrera, M; Miranda-Sepulveda, J; Rebolledo-Fuentes, M; Fierro, A.; Luhr, S; Iturriaga-Vasquez, P; CASSELS, BK; Reyes-Parada, M

Abstract

A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. © 2009 Elsevier Ltd. All rights reserved.

Más información

Título según WOS: Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors
Título según SCOPUS: Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors
Título de la Revista: BIOORGANIC & MEDICINAL CHEMISTRY
Volumen: 17
Número: 6
Editorial: PERGAMON-ELSEVIER SCIENCE LTD
Fecha de publicación: 2009
Página de inicio: 2452
Página final: 2460
Idioma: English
URL: http://linkinghub.elsevier.com/retrieve/pii/S0968089609001333
DOI:

10.1016/j.bmc.2009.01.074

Notas: ISI, SCOPUS