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

Year: 2002

Type: 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.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.50.1109

Authors: Axel Reinhard Stoit, Jos Hubertus Maria Lange, Arnold Peter den Hartog, Eric Ronken, Koos Tipker, Herman Heinrich van Stuivenberg, Jessica Adriana Rigtje Dijksman, Henri Cornelis Wals, Chris Gerrit Kruse

Language: English

Topic: Cannabis and Cannabinoid Research

Subfield: Pharmacology

Field: Medicine

Domain: Health Sciences

Open Access status: bronze

OpenAlex ID: W2156101406

FWCI: 2.62

Cites: 19

Cited by: 61

Related to: 10