Bioorg Med Chem Lett. 2003 Jan 6;13(1):69-73.

Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative.

Ooms F, Frédérick R, Durant F, Petzer JP, Castagnoli N, Van der Schyf CJ, Wouters J.

Source

Facultés Universitaires Notre-Dame de la Paix, Laboratoire de Chimie Moléculaire Structurale, B-5000 Namur, Belgium.

Abstract

The stereoelectronic properties of several potent reversible monoamine oxidase B (MAO-B) inhibitors were studied with a view to develop a pharmacophore model for reversible MAO-B inhibition. This study suggested that important specific H-bond and hydrophobic interactions are required for potent and selective MAO-B inhibition. These requirements were applied in the design and synthesis of a novel reversible and selective MAO-B inhibitor, 3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1,2-c]pyridazin-5-one, that is ca. 7000 times more selective as an inhibitor for MAO-B than for MAO-A, with K(i(MAO-B)) in the low nanomolar range.

PMID:: 12467619; [PubMed - indexed for MEDLINE]

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