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. 2002 Aug;50(8):1109-13.
doi: 10.1248/cpb.50.1109.

Design, Synthesis and Biological Activity of Rigid Cannabinoid CB1 Receptor Antagonists

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Design, Synthesis and Biological Activity of Rigid Cannabinoid CB1 Receptor Antagonists

Axel Reinhard Stoit et al. Chem Pharm Bull (Tokyo). .
Free article

Abstract

The design, synthesis and biological activities of potent pyrazole-based tricyclic CB1 receptor antagonists (2) are described. The key synthetic step involves the ring closure of the lithiated alpha, gamma-keto ester adduct (4). The optimal nitroderivative (28) in this series exhibits a high CB1 receptor affinity (pKi=7.2) as well as very potent antagonistic activity (pA2=8.8) in vitro. The regioselectivity of the pyrazole ring closure is shown to depend strongly on the aromatic substitution pattern of the applied arylhydrazine.

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