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.
MeSH terms
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Crystallography, X-Ray
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Humans
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Hydrophobic and Hydrophilic Interactions
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In Vitro Techniques
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Indenes / chemical synthesis*
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Indenes / chemistry
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Indenes / pharmacology
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Mitochondria, Liver / drug effects
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Mitochondria, Liver / enzymology
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Molecular Structure
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Monoamine Oxidase Inhibitors / chemical synthesis*
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Monoamine Oxidase Inhibitors / chemistry
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Monoamine Oxidase Inhibitors / pharmacology
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Pyridazines / chemical synthesis*
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Pyridazines / chemistry
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Pyridazines / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Indenes
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Monoamine Oxidase Inhibitors
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Pyridazines