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. 2005 Nov 1;15(21):4794-8.
doi: 10.1016/j.bmcl.2005.07.054.

Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity

Jos H M Lange  1 , Herman H van Stuivenberg, Willem Veerman, Henri C Wals, Bob Stork, Hein K A C Coolen, Andrew C McCreary, Tiny J P Adolfs, Chris G Kruse
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Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity

Jos H M Lange et al. Bioorg Med Chem Lett. .

Abstract

Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (Ki = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA2 = 8.8) and a high CB1/CB2 subtype selectivity (approximately 147-fold).

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