Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Role of the Furan in Affinity for Opioid Receptors

Thumbnail
View/Open
Issue Date
2009-09-21
Author
Simpson, Denise S.
Lovell, Kimberly M.
Lozama, Anthony
Han, Nina
Day, Victor W.
Dersch, Christina M.
Rothman, Richard B.
Prisinzano, Thomas E.
Publisher
Royal Society of Chemistry
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 3.0 (CC BY-NC-ND 3.0 US), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
Metadata
Show full item record
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.
URI
http://hdl.handle.net/1808/23216
DOI
https://doi.org/10.1039/b905148a
Collections
Citation
Simpson, D. S., Lovell, K. M., Lozama, A., Han, N., Day, V. W., Dersch, C. M., … Prisinzano, T. E. (2009). Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Role of the Furan in Affinity for Opioid Receptors. Organic & Biomolecular Chemistry, 7(18), 3748–3756. http://doi.org/10.1039/b905148a

Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.


We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.

This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 3.0 (CC BY-NC-ND 3.0 US), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
Except where otherwise noted, this item's license is described as: This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 3.0 (CC BY-NC-ND 3.0 US), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.