Literature DB >> 17303418

Convenient synthesis and in vitro pharmacological activity of 2-thioanalogs of salvinorins A and B.

Ruslan V Bikbulatov1, Feng Yan, Bryan L Roth, Jordan K Zjawiony.   

Abstract

To study drug-receptor interactions, new thio-derivatives of salvinorin A, an extremely potent natural kappa-opioid receptor (KOR) agonist, were synthesized. Obtained compounds were examined for receptor binding affinity. Analogs with the same configuration at carbon atom C-2 as in natural salvinorin A showed higher affinity to KOR than their corresponding epimers.

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Year:  2007        PMID： 17303418      PMCID： PMC1905843          DOI： 10.1016/j.bmcl.2007.01.100

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


  18 in total

1.  Synthesis and in vitro pharmacological studies of new C(4)-modified salvinorin A analogues.

Authors:  David Y W Lee; Minsheng He; Lee-Yuan Liu-Chen; Yulin Wang; Jian-Guo Li; Wei Xu; Zhongze Ma; William A Carlezon; Bruce Cohen
Journal:  Bioorg Med Chem Lett       Date:  2006-08-30       Impact factor: 2.823

2.  Synthesis of salvinorin A analogues as opioid receptor probes.

Authors:  Kevin Tidgewell; Wayne W Harding; Anthony Lozama; Howard Cobb; Kushal Shah; Pavitra Kannan; Christina M Dersch; Damon Parrish; Jeffrey R Deschamps; Richard B Rothman; Thomas E Prisinzano
Journal:  J Nat Prod       Date:  2006-06       Impact factor: 4.050

3.  Synthesis of 7beta-sulfur analogues of paclitaxel utilizing a novel epimerization of the 7alpha-thiol group.

Authors:  H Mastalerz; G Zhang; J Kadow; C Fairchild; B Long; D M Vyas
Journal:  Org Lett       Date:  2001-05-31       Impact factor: 6.005

4.  Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist.

Authors:  Thomas A Munro; Mark A Rizzacasa; Bryan L Roth; Beth A Toth; Feng Yan
Journal:  J Med Chem       Date:  2005-01-27       Impact factor: 7.446

5.  Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to kappa-opioid receptors.

Authors:  Feng Yan; Philip D Mosier; Richard B Westkaemper; Jeremy Stewart; Jordan K Zjawiony; Timothy A Vortherms; Douglas J Sheffler; Bryan L Roth
Journal:  Biochemistry       Date:  2005-06-21       Impact factor: 3.162

6.  Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum.

Authors:  L J Valdés; H M Chang; D C Visger; M Koreeda
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

7.  Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues.

Authors:  David Y W Lee; Minsheng He; Leelakrishna Kondaveti; Lee-Yuan Liu-Chen; Zhongze Ma; Yulin Wang; Yong Chen; Jian-Guo Li; Cecile Beguin; William A Carlezon; Bruce Cohen
Journal:  Bioorg Med Chem Lett       Date:  2005-10-01       Impact factor: 2.823

8.  Neoclerodane diterpenes as a novel scaffold for mu opioid receptor ligands.

Authors:  Wayne W Harding; Kevin Tidgewell; Nathan Byrd; Howard Cobb; Christina M Dersch; Eduardo R Butelman; Richard B Rothman; Thomas E Prisinzano
Journal:  J Med Chem       Date:  2005-07-28       Impact factor: 7.446

9.  A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A.

Authors:  Kevin Tidgewell; Wayne W Harding; Mark Schmidt; Kenneth G Holden; Daryl J Murry; Thomas E Prisinzano
Journal:  Bioorg Med Chem Lett       Date:  2004-10-18       Impact factor: 2.823

10.  Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations.

Authors:  Charles Chavkin; Sumit Sud; Wenzhen Jin; Jeremy Stewart; Jordan K Zjawiony; Daniel J Siebert; Beth Ann Toth; Sandra J Hufeisen; Bryan L Roth
Journal:  J Pharmacol Exp Ther       Date:  2004-01-08       Impact factor: 4.030
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  15 in total

Review 1.  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

Review 2.  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

Review 3.  A review of salvinorin analogs and their kappa-opioid receptor activity.

Authors:  Jeremy J Roach; Ryan A Shenvi
Journal:  Bioorg Med Chem Lett       Date:  2018-03-12       Impact factor: 2.823

4.  Synthesis and biological evaluation of new salvinorin A analogues incorporating natural amino acids.

Authors:  Jakub Fichna; Kevin Lewellyn; Feng Yan; Bryan L Roth; Jordan K Zjawiony
Journal:  Bioorg Med Chem Lett       Date:  2010-11-11       Impact factor: 2.823

5.  Kappa-opioid receptor-selective dicarboxylic ester-derived salvinorin A ligands.

Authors:  Prabhakar R Polepally; Kate White; Eyal Vardy; Bryan L Roth; Daneel Ferreira; Jordan K Zjawiony
Journal:  Bioorg Med Chem Lett       Date:  2013-04-04       Impact factor: 2.823

6.  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

7.  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

8.  Herkinorin analogues with differential beta-arrestin-2 interactions.

Authors:  Kevin Tidgewell; Chad E Groer; Wayne W Harding; Anthony Lozama; Matthew Schmidt; Alfred Marquam; Jessica Hiemstra; John S Partilla; Christina M Dersch; Richard B Rothman; Laura M Bohn; Thomas E Prisinzano
Journal:  J Med Chem       Date:  2008-04-02       Impact factor: 7.446

9.  Unusual hemiacetal structure derived from Salvinorin A.

Authors:  Paulo Carvalho; Ruslan Bikbulatov; Jordan K Zjawiony; Mitchell A Avery
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-28

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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