Literature DB >> 12443781

Novel 1',1'-chain substituted Delta(8)-tetrahydrocannabinols.

Demetris P Papahatjis1, Spyros P Nikas, Thanos Andreou, Alexandros Makriyannis.   

Abstract

1',1'-Cyclopropyl side chain substituents enhance the affinities of Delta(8)-tetrahydrocannabinol and respective cannabidiol analogues for the CB1 and CB2 cannabinoid receptors. The results support the hypothesis for a subsite within CB1 and CB2 binding domain at the level of the benzylic side chain carbon in the tetrahydrocannabinol and cannabidiol series. Efficient procedures for the synthesis of 1',1'-cyclopropyl analogues are described.

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Year:  2002        PMID: 12443781     DOI: 10.1016/s0960-894x(02)00785-0

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


  12 in total

1.  Novel 1',1'-chain substituted hexahydrocannabinols: 9β-hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a highly potent cannabinoid receptor 1 (CB1) agonist.

Authors:  Spyros P Nikas; Shakiru O Alapafuja; Ioannis Papanastasiou; Carol A Paronis; Vidyanand G Shukla; Demetris P Papahatjis; Anna L Bowman; Aneetha Halikhedkar; Xiuwen Han; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2010-10-14       Impact factor: 7.446

2.  AM2389, a high-affinity, in vivo potent CB1-receptor-selective cannabinergic ligand as evidenced by drug discrimination in rats and hypothermia testing in mice.

Authors:  Torbjörn U C Järbe; Sherrica Tai; Brian J LeMay; Spyros P Nikas; Vidyanand G Shukla; Alexander Zvonok; Alexandros Makriyannis
Journal:  Psychopharmacology (Berl)       Date:  2011-10-12       Impact factor: 4.530

3.  Heteroadamantyl cannabinoids.

Authors:  Darryl D Dixon; Divakaramenon Sethumadhavan; Tore Benneche; April R Banaag; Marcus A Tius; Ganesh A Thakur; Anna Bowman; Jodianne T Wood; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2010-08-12       Impact factor: 7.446

4.  Synthesis and characterization of a compact tricyclic resorcinol from (+)- and (-)-3-pinanol.

Authors:  Dai Lu; Spyros P Nikas; Xiu-Wen Han; Damon A Parrish; Alexandros Makriyannis
Journal:  Tetrahedron Lett       Date:  2012-08-29       Impact factor: 2.415

5.  The role of halogen substitution in classical cannabinoids: a CB1 pharmacophore model.

Authors:  Spyros P Nikas; Jolanta Grzybowska; Demetris P Papahatjis; Avgui Charalambous; Ali R Banijamali; Ravi Chari; Pusheng Fan; Therapia Kourouli; Sonyuan Lin; Albert J Nitowski; Gilbert Marciniak; Yan Guo; Xiuyan Li; Chia-Lin J Wang; Alexandros Makriyannis
Journal:  AAPS J       Date:  2004-10-19       Impact factor: 4.009

6.  Cannabidiol Inhibits Endocannabinoid Signaling in Autaptic Hippocampal Neurons.

Authors:  Alex Straiker; Michaela Dvorakova; Anaelle Zimmowitch; Ken Mackie
Journal:  Mol Pharmacol       Date:  2018-04-18       Impact factor: 4.436

7.  Controlled-deactivation cannabinergic ligands.

Authors:  Rishi Sharma; Spyros P Nikas; Carol A Paronis; Jodianne T Wood; Aneetha Halikhedkar; Jason Jianxin Guo; Ganesh A Thakur; Shashank Kulkarni; Othman Benchama; Jimit Girish Raghav; Roger S Gifford; Torbjörn U C Järbe; Jack Bergman; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2013-12-10       Impact factor: 7.446

8.  Probing the carboxyester side chain in controlled deactivation (-)-δ(8)-tetrahydrocannabinols.

Authors:  Spyros P Nikas; Rishi Sharma; Carol A Paronis; Shashank Kulkarni; Ganesh A Thakur; Dow Hurst; JodiAnne T Wood; Roger S Gifford; Girija Rajarshi; Yingpeng Liu; Jimit Girish Raghav; Jason Jianxin Guo; Torbjörn U C Järbe; Patricia H Reggio; Jack Bergman; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2014-12-16       Impact factor: 7.446

9.  The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation.

Authors:  Eric W Bow; John M Rimoldi
Journal:  Perspect Medicin Chem       Date:  2016-06-28

10.  Origin of Δ9-Tetrahydrocannabinol Impurity in Synthetic Cannabidiol.

Authors:  Cinzia Citti; Fabiana Russo; Pasquale Linciano; Sarah Sylvana Strallhofer; Francesco Tolomeo; Flavio Forni; Maria Angela Vandelli; Giuseppe Gigli; Giuseppe Cannazza
Journal:  Cannabis Cannabinoid Res       Date:  2021-02-12
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