Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Preparation and opioid receptor activity of salvinicin analogues

Denise S. Simpson, Peter L. Katavic, Anthony Lozama, Wayne W. Harding, Damon Parrish, Jeffrey R. Deschamps, Christina M. Dersch, John S. Partilla, Richard B. Rothman, Hernan Navarro, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Further modification of salvinorin A (1a), the major 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 that oxadiazole 11a and salvidivin A (12a), a photooxygenation product of 1a, have been identified as the first neoclerodane diterpenes with κ antagonist activity. This indicates that additional structural modifications of la may lead to analogues with higher potency and utility as drug abuse medications.

Original languageEnglish
Pages (from-to)3596-3603
Number of pages8
JournalJournal of Medicinal Chemistry
Volume50
Issue number15
DOIs
StatePublished - Jul 26 2007

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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