Neoclerodane diterpenes as a novel scaffold for mu opioid receptor ligands

J Med Chem. 2005 Jul 28;48(15):4765-71. doi: 10.1021/jm048963m.

Abstract

Structural modification of salvinorin A, the active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study a nonnitrogenous neoclerodane diterpene with mu opioid receptor affinity (13) that is an agonist at mu opioid receptors. This represents the identification of a novel structural class of mu opioid receptor agonists.

Publication types

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

MeSH terms

  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Diterpenes, Clerodane
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Furans / pharmacology
  • Humans
  • Ligands
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Pyrones / pharmacology
  • Radioligand Assay
  • Receptors, Opioid, delta / metabolism
  • Receptors, Opioid, kappa / metabolism
  • Receptors, Opioid, mu / agonists*
  • Salvia
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 9-(benzoyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho(2,1-c)pyran-7-carboxylic acid methyl ester
  • Diterpenes
  • Diterpenes, Clerodane
  • Furans
  • Ligands
  • Pyrones
  • Receptors, Opioid, delta
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • neoclerodane
  • salvinorin A