Issue 18, 2009
From the journal:

Organic & Biomolecular Chemistry

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

Denise S. Simpson,a   Kimberly M. Lovell,a   Anthony Lozama,ab   Nina Han,b   Victor W. Day,c   Christina M. Dersch,d   Richard B. Rothmand  and  Thomas E. Prisinzano*a  

* Corresponding authors

a Department of Medicinal Chemistry, The University of Kansas, Lawrence, USA
E-mail: prisinza@ku.edu
Fax: +1-785-864-5326
Tel: +1-785-864-3267

b Division of Medicinal & Natural Products Chemistry, The University of Iowa, Iowa City, IA, USA

c Department of Chemistry, The University of Kansas, Lawrence, KS, USA

d Clinical Psychopharmacology Section, IRP, NIDA, NIH, DHHS, Baltimore, MD, USA

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.

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

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Article information

DOI
https://doi.org/10.1039/B905148A
Article type
Paper
Submitted
13 Mar 2009
Accepted
08 Jun 2009
First published
14 Jul 2009

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

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

D. S. Simpson, K. M. Lovell, A. Lozama, N. Han, V. W. Day, C. M. Dersch, R. B. Rothman and T. E. Prisinzano, Org. Biomol. Chem., 2009, 7, 3748 DOI: 10.1039/B905148A

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