Literature DB >> 21115248

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

Jakub Fichna1, Kevin Lewellyn, Feng Yan, Bryan L Roth, Jordan K Zjawiony.   

Abstract

The synthesis and in vitro evaluation of a new series of salvinorin A analogues substituted at the C(2) position with natural amino acids is reported. Compound 12, containing Val, displayed high affinity and full agonist activity at the kappa-opioid receptor. Analogues with bulky and/or aromatic residues were inactive, showing the importance of size and electronegativity of C(2)-substituents for binding affinity of salvinorin A derivatives.
Copyright © 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 21115248      PMCID： PMC3031978          DOI： 10.1016/j.bmcl.2010.11.046

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


  12 in total

1.  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

2.  Synthesis and in vitro evaluation of salvinorin A analogues: effect of configuration at C(2) and substitution at C(18).

Authors:  Cécile Béguin; Michele R Richards; Jian-Guo Li; Yulin Wang; Wei Xu; Lee-Yuan Liu-Chen; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem Lett       Date:  2006-06-13       Impact factor: 2.823

3.  Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2).

Authors:  Cécile Béguin; Michele R Richards; Yulin Wang; Yong Chen; Lee-Yuan Liu-Chen; Zhongze Ma; David Y W Lee; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem Lett       Date:  2005-06-02       Impact factor: 2.823

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

Authors:  Ruslan V Bikbulatov; Feng Yan; Bryan L Roth; Jordan K Zjawiony
Journal:  Bioorg Med Chem Lett       Date:  2007-02-02       Impact factor: 2.823

5.  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

6.  Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers.

Authors:  Thomas A Munro; Katharine K Duncan; Wei Xu; Yulin Wang; Lee-Yuan Liu-Chen; William A Carlezon; Bruce M Cohen; Cécile Béguin
Journal:  Bioorg Med Chem       Date:  2007-10-24       Impact factor: 3.641

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

Review 8.  Selective natural kappa opioid and cannabinoid receptor agonists with a potential role in the treatment of gastrointestinal dysfunction.

Authors:  Jakub Fichna; Rudolf Schicho; Anna Janecka; Jordan K Zjawiony; Martin Storr
Journal:  Drug News Perspect       Date:  2009-09

9.  2-Methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A.

Authors:  Yulin Wang; Yong Chen; Wei Xu; David Y W Lee; Zhongze Ma; Scott M Rawls; Alan Cowan; Lee-Yuan Liu-Chen
Journal:  J Pharmacol Exp Ther       Date:  2007-12-18       Impact factor: 4.030

10.  Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.

Authors:  Bryan L Roth; Karen Baner; Richard Westkaemper; Daniel Siebert; Kenner C Rice; SeAnna Steinberg; Paul Ernsberger; Richard B Rothman
Journal:  Proc Natl Acad Sci U S A       Date:  2002-08-21       Impact factor: 11.205
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  3 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.  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

3.  Michael acceptor approach to the design of new salvinorin A-based high affinity ligands for the kappa-opioid receptor.

Authors:  Prabhakar R Polepally; Krzysztof Huben; Eyal Vardy; Vincent Setola; Philip D Mosier; Bryan L Roth; Jordan K Zjawiony
Journal:  Eur J Med Chem       Date:  2014-08-23       Impact factor: 6.514
  3 in total

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