Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Role of the furan in affinity for opioid receptors

Denise S. Simpson, Kimberly M. Lovell, Anthony Lozama, Nina Han, Victor W. Day, Christina M. Dersch, Richard B. Rothman, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Further synthetic modification of the furan ring of salvinorin A (1), the major active component of Salvia divinorum, has resulted in novel neoclerodane diterpenes with opioid receptor affinity and activity. A computational study has predicted 1 to be a reproductive toxicant in mammals and is suggestive that use of 1 may be associated with adverse effects. We report in this study that piperidine 21 and thiomorpholine 23 have been identified as selective partial agonists at kappa opioid receptors. This indicates that additional structural modifications of 1 may provide ligands with good selectivity for opioid receptors but with reduced potential for toxicity.

Original languageEnglish
Pages (from-to)3748-3756
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number18
DOIs
StatePublished - 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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