Literature DB >> 27152055

An alternative synthesis and x-ray crystallographic confirmation of (-)-stepholidine.

Satishkumar V Gadhiya1, Chunhua Hu2, Wayne W Harding3.   

Abstract

A formal enantioselective synthesis of (-)-stepholidine that provides an alternative preparation of key lactone intermediate 2 is described. The stereostructure of (-)-stepholidine prepared via this method was confirmed by x-ray diffraction.

Entities:  

Keywords:  Dopamine; Stepholidine; THPB; Tetrahydroprotoberberine; X-ray crystallography

Year:  2016        PMID： 27152055      PMCID： PMC4852479          DOI： 10.1016/j.tetlet.2016.03.108

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  9 in total

Review 1.  (-)-Stepholidine: a potential novel antipsychotic drug with dual D1 receptor agonist and D2 receptor antagonist actions.

Authors:  Guo-Zhang Jin; Zi-Tao Zhu; Yu Fu
Journal:  Trends Pharmacol Sci       Date:  2002-01       Impact factor: 14.819

2.  Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors.

Authors:  Sébastien Albrecht; Albert Defoin; Emmanuel Salomon; Céline Tarnus; Anders Wetterholm; Jasper Z Haeggström
Journal:  Bioorg Med Chem       Date:  2006-07-17       Impact factor: 3.641

3.  Enantioselective total synthesis of (-)-(S)-stepholidine.

Authors:  Jian-Jun Cheng; Yu-She Yang
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

4.  Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids.

Authors:  M Hanaoka; T Hirasawa; W J Cho; S Yasuda
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-03       Impact factor: 1.645

5.  The dopamine D1 receptor agonist and D2 receptor antagonist LEK-8829 attenuates reinstatement of cocaine-seeking in rats.

Authors:  Natasa Milivojevic; Igor Krisch; Dusan Sket; Marko Zivin
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2004-05-07       Impact factor: 3.000

6.  Tetrahydroprotoberberine--a new chemical type of antagonist of dopamine receptors.

Authors:  G Z Jin; X L Wang; W X Shi
Journal:  Sci Sin B       Date:  1986-05

7.  The antipsychotic potential of l-stepholidine--a naturally occurring dopamine receptor D1 agonist and D2 antagonist.

Authors:  Sridhar Natesan; Greg E Reckless; Karen B L Barlow; John Odontiadis; José N Nobrega; Glen B Baker; Susan R George; David Mamo; Shitij Kapur
Journal:  Psychopharmacology (Berl)       Date:  2008-06-03       Impact factor: 4.530

8.  2,3,9- and 2,3,11-trisubstituted tetrahydroprotoberberines as D2 dopaminergic ligands.

Authors:  Javier Párraga; Nuria Cabedo; Sebastián Andujar; Laura Piqueras; Laura Moreno; Abraham Galán; Emilio Angelina; Ricardo D Enriz; María Dolores Ivorra; María Jesús Sanz; Diego Cortes
Journal:  Eur J Med Chem       Date:  2013-08-11       Impact factor: 6.514

9.  The neuropharmacology of (-)-stepholidine and its potential applications.

Authors:  Kechun Yang; Guozhang Jin; Jie Wu
Journal:  Curr Neuropharmacol       Date:  2007-12       Impact factor: 7.363
  9 in total
  2 in total

1.  (-)-Stepholidine blocks expression, but not development, of cocaine conditioned place preference in rats.

Authors:  A Bennett; E Barrera; H Namballa; W Harding; R Ranaldi
Journal:  Neurosci Lett       Date:  2020-06-09       Impact factor: 3.046

Review 2.  Deep Learning in Drug Discovery and Medicine; Scratching the Surface.

Authors:  Dibyendu Dana; Satishkumar V Gadhiya; Luce G St Surin; David Li; Farha Naaz; Quaisar Ali; Latha Paka; Michael A Yamin; Mahesh Narayan; Itzhak D Goldberg; Prakash Narayan
Journal:  Molecules       Date:  2018-09-18       Impact factor: 4.411
  2 in total

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