Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues

Bioorg Med Chem Lett. 2005 Aug 15;15(16):3744-7. doi: 10.1016/j.bmcl.2005.05.048.

Abstract

Salvinorin A is the most potent naturally occurring opioid agonist yet discovered with high selectivity and affinity for kappa-opioid receptor. To explore its structure and activity relationships, a series of salvinorin A derivatives modified at the C2 position were prepared and studied. These salvinorin A derivatives were screened for binding and functional activities at the human kappa-opioid receptor. Compound 4, containing a methoxymethyl group at the 2-position, was a full kappa-agonist with an EC50 value at 0.6 nM, which is about 7 times more potent than salvinorin A.

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Diterpenes, Clerodane
  • Humans
  • Molecular Conformation
  • Receptors, Opioid, kappa / agonists
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • Diterpenes, Clerodane
  • Receptors, Opioid, kappa
  • salvinorin A