Abstract
Based on the bioisosteric replacement of the pyrazole C3-carboxamide of rimonabant with a 5-alkyl oxadiazole ring, a novel class of oxadiazole derivatives with promising biological activity towards CB1 receptors was discovered. Among them, compounds with an alkyl linker containing a strong electron-withdrawing group (e.g., CF(3)) and a sterically favorable bulky group (e.g., t-butyl) exhibited excellent CB1 antagonism and selectivity, and thus might serve as potential candidates for further development as anti-obesity agents.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemistry*
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Amides / metabolism*
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Cell Line
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Humans
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Isomerism
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Molecular Structure
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Piperidines / chemistry*
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Piperidines / metabolism*
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Pyrazoles / chemistry*
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Pyrazoles / metabolism*
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Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
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Receptor, Cannabinoid, CB1 / metabolism
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Receptor, Cannabinoid, CB2 / antagonists & inhibitors*
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Receptor, Cannabinoid, CB2 / metabolism
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Rimonabant
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Structure-Activity Relationship
Substances
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Amides
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Piperidines
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Pyrazoles
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Receptor, Cannabinoid, CB1
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Receptor, Cannabinoid, CB2
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pyrazole
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Rimonabant