Abstract
Structure-activity relationship studies were employed to synthesize a series of 3- and 3,4-substituted benzamides from 3-amino-2-cyclohexenones. An improved method for the synthesis of benzamides from 3-amino-2-cyclohexenones is presented which provided significantly higher yields (71-79%) for the reported compounds. NMR and X-ray structural analyses were undertaken to note the possible intra- and intermolecular interactions of the synthesized analogs. Molecular modeling studies were used to determine the minimized configuration and were compared to their X-ray structures for correlation. These new entities were evaluated as potential anticonvulsants and type IV phosphodiesterase inhibitors (PDE4).
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors*
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3',5'-Cyclic-AMP Phosphodiesterases / metabolism
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Animals
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Anticonvulsants / chemical synthesis*
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Anticonvulsants / chemistry
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Anticonvulsants / pharmacology*
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Benzamides / chemical synthesis
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Benzamides / chemistry*
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Benzamides / pharmacology*
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Crystallography, X-Ray
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Cyclic Nucleotide Phosphodiesterases, Type 4
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Mice
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Molecular Structure
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Structure-Activity Relationship
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Vinyl Compounds / chemical synthesis*
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Vinyl Compounds / chemistry
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Vinyl Compounds / pharmacology*
Substances
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Anticonvulsants
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Benzamides
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Enzyme Inhibitors
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Vinyl Compounds
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benzamide
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3',5'-Cyclic-AMP Phosphodiesterases
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Cyclic Nucleotide Phosphodiesterases, Type 4