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Issue 18, 2008
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Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists

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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., CF3) 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.

Graphical abstract: Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists

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Publication details

The article was received on 06 May 2008, accepted on 20 Jun 2008 and first published on 23 Jul 2008


Article type: Paper
DOI: 10.1039/B807648K
Citation: Org. Biomol. Chem., 2008,6, 3399-3407
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    Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists

    C. Chu, M. Hung, M. Hsieh, C. Kuo, S. T. D., J. Song, H. Chiu, Y. Chao and K. Shia, Org. Biomol. Chem., 2008, 6, 3399
    DOI: 10.1039/B807648K

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