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Scaffold hopping strategy toward original pyrazolines as selective CB₂ receptor ligands.

Abstract：

:In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB(2) receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [(35)S]-GTPγS binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure-activity relationship.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Gembus V,Furman C,Millet R,Mansouri R,Chavatte P,Levacher V,Brière JF

doi

10.1016/j.ejmech.2012.10.031

subject

Has Abstract

pub_date

2012-12-01 00:00:00

pages

396-404

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(12)00635-6

journal_volume

58

pub_type

杂志文章

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