Literature DB >> 20187040

Design and synthesis of (13S)-methyl-substituted arachidonic acid analogues: templates for novel endocannabinoids.

Demetris P Papahatjis1, Victoria R Nahmias, Spyros P Nikas, Marion Schimpgen, Alexandros Makriyannis.   

Abstract

Two novel methyl-substituted arachidonic acid derivatives were prepared in an enantioselective manner from commercially available chiral building blocks, and were found to be excellent templates for the development of (13S)-methyl-substituted anandamide analogues. One of the compounds synthesized, namely, (13S,5Z,8Z,11Z,14Z)-13-methyl-eicosa-5,8,11,14-tetraenoic acid N-(2-hydroxyethyl)amide, is an endocannabinoid analogue with remarkably high affinity for the CB1 cannabinoid receptor.

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Year:  2010        PMID： 20187040      PMCID： PMC3786736          DOI： 10.1002/chem.200902880

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  64 in total

1.  Oxygenation of the endocannabinoid, 2-arachidonylglycerol, to glyceryl prostaglandins by cyclooxygenase-2.

Authors:  K R Kozak; S W Rowlinson; L J Marnett
Journal:  J Biol Chem       Date:  2000-10-27       Impact factor: 5.157

2.  Stereochemical selectivity of methanandamides for the CB1 and CB2 cannabinoid receptors and their metabolic stability.

Authors:  A Goutopoulos; P Fan; A D Khanolkar; X Q Xie; S Lin; A Makriyannis
Journal:  Bioorg Med Chem       Date:  2001-07       Impact factor: 3.641

3.  Observational analysis of feeding induced by Delta9-THC and anandamide.

Authors:  Claire M Williams; Tim C Kirkham
Journal:  Physiol Behav       Date:  2002-06-01

4.  Involvement of the cAMP/protein kinase A pathway and of mitogen-activated protein kinase in the anti-proliferative effects of anandamide in human breast cancer cells.

Authors:  D Melck; D Rueda; I Galve-Roperh; L De Petrocellis; M Guzmán; V Di Marzo
Journal:  FEBS Lett       Date:  1999-12-17       Impact factor: 4.124

5.  An endogenous cannabinoid (2-AG) is neuroprotective after brain injury.

Authors:  D Panikashvili; C Simeonidou; S Ben-Shabat; L Hanus; A Breuer; R Mechoulam; E Shohami
Journal:  Nature       Date:  2001-10-04       Impact factor: 49.962

6.  Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase.

Authors:  Mario van der Stelt; J Albert van Kuik; Monica Bari; Guus van Zadelhoff; Bas R Leeflang; Gerrit A Veldink; Alessandro Finazzi-Agrò; Johannes F G Vliegenthart; Mauro Maccarrone
Journal:  J Med Chem       Date:  2002-08-15       Impact factor: 7.446

7.  Conformational memories and the endocannabinoid binding site at the cannabinoid CB1 receptor.

Authors:  Judy Barnett-Norris; Dow P Hurst; Diane L Lynch; Frank Guarnieri; Alex Makriyannis; Patricia H Reggio
Journal:  J Med Chem       Date:  2002-08-15       Impact factor: 7.446

8.  Brain monoglyceride lipase participating in endocannabinoid inactivation.

Authors:  T P Dinh; D Carpenter; F M Leslie; T F Freund; I Katona; S L Sensi; S Kathuria; D Piomelli
Journal:  Proc Natl Acad Sci U S A       Date:  2002-07-22       Impact factor: 11.205

Review 9.  Oxidative metabolism of endocannabinoids.

Authors:  K R Kozak; L J Marnett
Journal:  Prostaglandins Leukot Essent Fatty Acids       Date:  2002 Feb-Mar       Impact factor: 4.006

Review 10.  The endocannabinoid system: its general strategy of action, tools for its pharmacological manipulation and potential therapeutic exploitation.

Authors:  Vincenzo Di Marzo
Journal:  Pharmacol Res       Date:  2009-03-04       Impact factor: 7.658
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  6 in total

Review 1.  Terpenes and lipids of the endocannabinoid and transient-receptor-potential-channel biosignaling systems.

Authors:  David R Janero; Alexandros Makriyannis
Journal:  ACS Chem Neurosci       Date:  2014-06-05       Impact factor: 4.418

2.  Application of Chemoenzymatic Hydrolysis in the Synthesis of 2-Monoacylglycerols.

Authors:  Kyle M Whitten; Alexandros Makriyannis; Subramanian K Vadivel
Journal:  Tetrahedron       Date:  2012-05-05       Impact factor: 2.457

3.  C-ring cannabinoid lactones: a novel cannabinergic chemotype.

Authors:  Rishi Sharma; Spyros P Nikas; Jason Jianxin Guo; Srikrishnan Mallipeddi; JodiAnne T Wood; Alexandros Makriyannis
Journal:  ACS Med Chem Lett       Date:  2014-01-14       Impact factor: 4.345

4.  Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s).

Authors:  Erin L Shelnut; Spyros P Nikas; David F Finnegan; Nan Chiang; Charles N Serhan; Alexandros Makriyannis
Journal:  Tetrahedron Lett       Date:  2015-03-11       Impact factor: 2.415

5.  Enantioselective synthesis of (10S)- and (10R)-methyl-anandamides.

Authors:  Spyros P Nikas; Marsha D'Souza; Alexandros Makriyannis
Journal:  Tetrahedron       Date:  2012-08-05       Impact factor: 2.457

6.  Novel tail and head group prostamide probes.

Authors:  David F Finnegan; Erin L Shelnut; Spyros P Nikas; Nan Chiang; Charles N Serhan; Alexandros Makriyannis
Journal:  Bioorg Med Chem Lett       Date:  2015-02-04       Impact factor: 2.823
  6 in total

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