Literature DB >> 16621556

Synthetic studies of neoclerodane diterpenes from Salvia divinorum: selective modification of the furan ring.

Wayne W Harding1, Matthew Schmidt, Kevin Tidgewell, Pavitra Kannan, Kenneth G Holden, Christina M Dersch, Richard B Rothman, Thomas E Prisinzano.   

Abstract

A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at kappa opioid receptors.

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Year:  2006        PMID： 16621556     DOI： 10.1016/j.bmcl.2006.03.062

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  24 in total

Review 1.  Clerodane diterpenes: sources, structures, and biological activities.

Authors:  Rongtao Li; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Nat Prod Rep       Date:  2016-07-18       Impact factor: 13.423

Review 2.  Ethnobotany as a pharmacological research tool and recent developments in CNS-active natural products from ethnobotanical sources.

Authors:  Will C McClatchey; Gail B Mahady; Bradley C Bennett; Laura Shiels; Valentina Savo
Journal:  Pharmacol Ther       Date:  2009-05-05       Impact factor: 12.310

3.  Structure-based design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the kappa-opioid receptor.

Authors:  Feng Yan; Ruslan V Bikbulatov; Viorel Mocanu; Nedyalka Dicheva; Carol E Parker; William C Wetsel; Philip D Mosier; Richard B Westkaemper; John A Allen; Jordan K Zjawiony; Bryan L Roth
Journal:  Biochemistry       Date:  2009-07-28       Impact factor: 3.162

Review 4.  Salvinorin A analogs as probes in opioid pharmacology.

Authors:  Thomas E Prisinzano; Richard B Rothman
Journal:  Chem Rev       Date:  2008-05       Impact factor: 60.622

5.  Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of Opioid Receptor affinity.

Authors:  Gianfranco Fontana; Giuseppe Savona; Benjamín Rodríguez; Christina M Dersch; Richard B Rothman; Thomas E Prisinzano
Journal:  Tetrahedron       Date:  2008-12-20       Impact factor: 2.457

Review 6.  Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A.

Authors:  Christopher W Cunningham; Richard B Rothman; Thomas E Prisinzano
Journal:  Pharmacol Rev       Date:  2011-03-28       Impact factor: 25.468

7.  Modification of the furan ring of salvinorin A: identification of a selective partial agonist at the kappa opioid receptor.

Authors:  Cécile Béguin; Katharine K Duncan; Thomas A Munro; Douglas M Ho; Wei Xu; Lee-Yuan Liu-Chen; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem       Date:  2008-12-14       Impact factor: 3.641

8.  Revised structure of deacetyl-1,10-didehydrosalvinorin G.

Authors:  Zhongze Ma; David Y W Lee
Journal:  Tetrahedron Lett       Date:  2007-07-30       Impact factor: 2.415

9.  CoMFA analyses of C-2 position salvinorin A analogs at the kappa-opioid receptor provides insights into epimer selectivity.

Authors:  Donna L McGovern; Philip D Mosier; Bryan L Roth; Richard B Westkaemper
Journal:  J Mol Graph Model       Date:  2010-01-04       Impact factor: 2.518

10.  Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Authors:  Zhongze Ma; David Y W Lee
Journal:  Tetrahedron Lett       Date:  2008-03-10       Impact factor: 2.415
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