Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)

Bioorg Med Chem Lett. 2005 Jun 2;15(11):2761-5. doi: 10.1016/j.bmcl.2005.03.113.

Abstract

Salvinorin A is the only known non-nitrogenous and specific kappa-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the kappa-opioid receptor. Unsubstituted carbamate 9 was a potent kappa-agonist (EC(50) = 6.2 nM) and should be more stable than salvinorin A toward metabolic transformations. Compound 10, containing an N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • CHO Cells
  • Cricetinae
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Diterpenes, Clerodane
  • Drug Evaluation, Preclinical

Substances

  • Diterpenes
  • Diterpenes, Clerodane
  • salvinorin A