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. 2006 Sep 1;16(17):4679-85.
doi: 10.1016/j.bmcl.2006.05.093. Epub 2006 Jun 13.

Synthesis and in vitro evaluation of salvinorin A analogues: effect of configuration at C(2) and substitution at C(18)

Cécile Béguin  1 , Michele R Richards, Jian-Guo Li, Yulin Wang, Wei Xu, Lee-Yuan Liu-Chen, William A Carlezon Jr, Bruce M Cohen
Affiliations

Synthesis and in vitro evaluation of salvinorin A analogues: effect of configuration at C(2) and substitution at C(18)

Cécile Béguin et al. Bioorg Med Chem Lett. .

Erratum in

  • Bioorg Med Chem Lett. 2008 Aug 1;18(15):4448

Abstract

kappa-opioid receptor ligands have raised interest for their apparent effects on mood. The potent and selective kappa-agonist salvinorin A has short-lasting (15min) depressive-like effects in rats in behavioral models used to study mood disorders. Two series of salvinorin derivatives modified at C(2) and C(18), respectively, were synthesized and their kappa-opioid receptor affinities, potencies, and efficacies were evaluated using in vitro receptor binding and biochemical functional assays. Modification at C(2) yielded potent kappa-agonists that are predicted to have improved metabolic stability (14a, 15a) or increased water solubility (10b). Our preliminary SAR study at C(18) suggested that this part of the molecule interacts with a tight lipophilic pocket of the kappa-receptor.

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