Literature DB >> 19679471

Chemical methods for the synthesis and modification of neoclerodane diterpenes.

Anthony Lozama1, Thomas E Prisinzano.   

Abstract

Diterpenes are a structural class of molecules that are derived from four isoprene subunits and are widespread throughout nature. A number of neoclerodane diterpenes have been found to have biological activity but a limited number of chemical investigations have been conducted. Recently, the neoclerodane diterpene, salvinorin A (12) has been investigated due to its unique pharmacological profile. This review will discuss the chemical methods used to chemically modify and synthesize 12.

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Year:  2009        PMID： 19679471      PMCID： PMC2977960          DOI： 10.1016/j.bmcl.2009.07.069

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


  48 in total

Review 1.  Deoxyxylulose phosphate pathway to terpenoids.

Authors:  W Eisenreich; F Rohdich; A Bacher
Journal:  Trends Plant Sci       Date:  2001-02       Impact factor: 18.313

2.  Total Synthesis of Clerocidin via a Novel, Enantioselective Homoallenylboration Methodology.

Authors:  Alan X. Xiang; Donald A. Watson; Taotao Ling; Emmanuel A. Theodorakis
Journal:  J Org Chem       Date:  1998-10-02       Impact factor: 4.354

3.  The isoprene rule and the biogenesis of terpenic compounds.

Authors:  L RUZICKA
Journal:  Experientia       Date:  1953-10-15

4.  Autoxidation of salvinorin A under basic conditions.

Authors:  Thomas A Munro; Glenn W Goetchius; Bryan L Roth; Timothy A Vortherms; Mark A Rizzacasa
Journal:  J Org Chem       Date:  2005-11-25       Impact factor: 4.354

5.  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

6.  Ethnopharmacology of ska María Pastora (Salvia divinorum, Epling and Játiva-M.).

Authors:  L J Valdés; J L Díaz; A G Paul
Journal:  J Ethnopharmacol       Date:  1983-05       Impact factor: 4.360

7.  Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum.

Authors:  Wayne W Harding; Kevin Tidgewell; Matthew Schmidt; Kushal Shah; Christina M Dersch; John Snyder; Damon Parrish; Jeffrey R Deschamps; Richard B Rothman; Thomas E Prisinzano
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

8.  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

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.  Characterization of aspen isoprene synthase, an enzyme responsible for leaf isoprene emission to the atmosphere.

Authors:  G M Silver; R Fall
Journal:  J Biol Chem       Date:  1995-06-02       Impact factor: 5.157
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  7 in total

Review 1.  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

2.  Semisynthetic neoclerodanes as kappa opioid receptor probes.

Authors:  Kimberly M Lovell; Tamara Vasiljevik; Juan J Araya; Anthony Lozama; Katherine M Prevatt-Smith; Victor W Day; Christina M Dersch; Richard B Rothman; Eduardo R Butelman; Mary Jeanne Kreek; Thomas E Prisinzano
Journal:  Bioorg Med Chem       Date:  2012-03-01       Impact factor: 3.641

Review 3.  Kinase cascades and ligand-directed signaling at the kappa opioid receptor.

Authors:  Michael R Bruchas; Charles Chavkin
Journal:  Psychopharmacology (Berl)       Date:  2010-04-17       Impact factor: 4.530

4.  Blocking Deprotonation with Retention of Aromaticity in a Plant ent-Copalyl Diphosphate Synthase Leads to Product Rearrangement.

Authors:  Kevin C Potter; Jiachen Zi; Young J Hong; Samuel Schulte; Brandi Malchow; Dean J Tantillo; Reuben J Peters
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-25       Impact factor: 15.336

Review 5.  Biologically Active Diterpenoids in the Clerodendrum Genus-A Review.

Authors:  Łukasz Kuźma; Jan Gomulski
Journal:  Int J Mol Sci       Date:  2022-09-20       Impact factor: 6.208

6.  Stereoselective chemo-enzymatic oxidation routes for (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene.

Authors:  Christian Görner; Max Hirte; Stephanie Huber; Patrick Schrepfer; Thomas Brück
Journal:  Front Microbiol       Date:  2015-10-13       Impact factor: 5.640

7.  Evaluation of morphine-like effects of the mixed mu/delta agonist morphine-6-O-sulfate in rats: Drug discrimination and physical dependence.

Authors:  Jai Shankar K Yadlapalli; Shoban Babu Bommagani; Ryan D Mahelona; Anqi Wan; Brenda M Gannon; Narsimha R Penthala; Maxim Dobretsov; Peter A Crooks; William E Fantegrossi
Journal:  Pharmacol Res Perspect       Date:  2018-06-19
  7 in total

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