Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5H-indeno[1,2-c]pyridazin-5-one core

R. Frédérick, W. Dumont, F. Ooms, L. Aschenbach, C.J. Van Der Schyf, N. Castagnoli, J. Wouters, A. Krief

Research output: Contribution to journalArticle

Abstract

The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[1,2-c]pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C(8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[1,2-c]pyridazin-5-one core at C(7) vs C(8) dramatically influences the MAO-inhibiting properties of these compounds.
Original languageEnglish
Pages (from-to)3743-3747
Number of pages5
JournalJournal of Medicinal Chemistry
Volume49
Issue number12
DOIs
Publication statusPublished - 15 Jun 2006

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  • Datasets

    CCDC 282947: Experimental Crystal Structure Determination

    Aschenbach, L. (Contributor), Castagnoli, N. (Contributor), Dumont, W. (Contributor), FREDERICK, R. (Contributor), KRIEF, A. (Contributor), Ooms, F. (Contributor), Van der Schyf, C. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007

    Dataset

    CCDC 282948: Experimental Crystal Structure Determination

    Aschenbach, L. (Contributor), Castagnoli, N. (Contributor), Dumont, W. (Contributor), FREDERICK, R. (Contributor), KRIEF, A. (Contributor), Ooms, F. (Contributor), Van der Schyf, C. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007

    Dataset

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