Abstract
N-Benzyl- and N-propargyl-1H-pyrrole-2-carboxyamides and some related methylenamines were synthesized and tested for their monoamine oxidase types A and B inhibitory activity. 2-(N-Methyl-N-propargylaminomethyl)-1H-pyrrole (24) was the most potent MAO-A inhibitor of the series [K(i)(MAO-A) = 0.0054 microM], but it was not selective. Inhibitors N-4-fluorobenzyl-1H-pyrrole-2-carboxamide (12) and N-cyclohexylmethyl-1H-pyrrole-2-carboxamide (25) showed the highest MAO-A selectivity indexes (SI) corresponding to 2025 and >2500, respectively, while 2-(N-methyl-N-benzylaminomethyl)-1H-pyrrole (21) was the most selective MAO-B inhibitor, having an SI of 0.0057.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemical synthesis*
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Alkynes / chemistry
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Alkynes / pharmacology
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Amides / chemical synthesis
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Amides / chemistry
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Amides / pharmacology
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Amines / chemical synthesis
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Amines / chemistry
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Amines / pharmacology
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Animals
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Brain / enzymology
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Brain / ultrastructure
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Cattle
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Isoenzymes / metabolism
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Mitochondria / enzymology
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Monoamine Oxidase / metabolism*
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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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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Pyrroles / pharmacology
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Structure-Activity Relationship
Substances
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Alkynes
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Amides
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Amines
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Isoenzymes
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Monoamine Oxidase Inhibitors
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Pyrroles
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Monoamine Oxidase