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

doi:10.1039/B905148A

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Organic & Biomolecular Chemistry

Issue 18, 2009

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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 and Thomas E. Prisinzano

Org. Biomol. Chem., 2009, 7, 3748-3756

DOI: 10.1039/B905148A
Received 13 Mar 2009, Accepted 08 Jun 2009
First published on the web 14 Jul 2009

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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.

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Preparation of 4–19, 22, and 24–30; HPLC analyses of 4–32 and 34–36
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Denise S. Simpson
Kimberly M. Lovell
Anthony Lozama
Nina Han
Victor W. Day
Christina M. Dersch
Richard B. Rothman
Thomas E. Prisinzano

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Organic & Biomolecular Chemistry

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

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