Literature DB >> 20593789

Heteroadamantyl cannabinoids.

Darryl D Dixon1, Divakaramenon Sethumadhavan, Tore Benneche, April R Banaag, Marcus A Tius, Ganesh A Thakur, Anna Bowman, Jodianne T Wood, Alexandros Makriyannis.   

Abstract

The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.

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Year:  2010        PMID： 20593789      PMCID： PMC3699191          DOI： 10.1021/jm100390h

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  29 in total

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

Authors:  Demetris P Papahatjis; Spyros P Nikas; Thanos Andreou; Alexandros Makriyannis
Journal:  Bioorg Med Chem Lett       Date:  2002-12-16       Impact factor: 2.823

2.  Behavioral effects of the novel cannabinoid full agonist AM 411.

Authors:  Peter J McLaughlin; Dai Lu; Keisha M Winston; Ganesh Thakur; Lynn A Swezey; Alexandros Makriyannis; John D Salamone
Journal:  Pharmacol Biochem Behav       Date:  2005-04-21       Impact factor: 3.533

3.  Delta(9)-THC stimulates food intake in Lewis rats: effects on chow, high-fat and sweet high-fat diets.

Authors:  J E Koch
Journal:  Pharmacol Biochem Behav       Date:  2001-03       Impact factor: 3.533

4.  2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: highly efficient organocatalysts for oxidation of alcohols.

Authors:  Masatoshi Shibuya; Masaki Tomizawa; Iwao Suzuki; Yoshiharu Iwabuchi
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

5.  Structure-activity relationships for 1',1'-dimethylalkyl-Delta8-tetrahydrocannabinols.

Authors:  John W Huffman; John R A Miller; John Liddle; Shu Yu; Brian F Thomas; Jenny L Wiley; Billy R Martin
Journal:  Bioorg Med Chem       Date:  2003-04-03       Impact factor: 3.641

6.  Oxaza adamantyl cannabinoids. A new class of cannabinoid receptor probes.

Authors:  David Le Goanvic; Marcus A Tius
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

7.  R(+)-methanandamide and other cannabinoids induce the expression of cyclooxygenase-2 and matrix metalloproteinases in human nonpigmented ciliary epithelial cells.

Authors:  Susanne Rösch; Robert Ramer; Kay Brune; Burkhard Hinz
Journal:  J Pharmacol Exp Ther       Date:  2005-12-05       Impact factor: 4.030

8.  Total synthesis of mycalamide A.

Authors:  Jeong-Hun Sohn; Nobuaki Waizumi; H Marlon Zhong; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

Review 9.  Cannabinoids in the treatment of pain and spasticity in multiple sclerosis.

Authors:  Paul F Smith
Journal:  Curr Opin Investig Drugs       Date:  2002-06

Review 10.  Cannabinoids in the treatment of glaucoma.

Authors:  Tomi Järvinen; David W Pate; Krista Laine
Journal:  Pharmacol Ther       Date:  2002-08       Impact factor: 12.310
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  13 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.  Novel adamantyl cannabinoids as CB1 receptor probes.

Authors:  Ganesh A Thakur; Shama Bajaj; Carol Paronis; Yan Peng; Anna L Bowman; Lawrence S Barak; Marc G Caron; Demon Parrish; Jeffrey R Deschamps; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2013-05-14       Impact factor: 7.446

3.  Mapping Cannabinoid 1 Receptor Allosteric Site(s): Critical Molecular Determinant and Signaling Profile of GAT100, a Novel, Potent, and Irreversibly Binding Probe.

Authors:  Robert B Laprairie; Abhijit R Kulkarni; Pushkar M Kulkarni; Dow P Hurst; Diane Lynch; Patricia H Reggio; David R Janero; Roger G Pertwee; Lesley A Stevenson; Melanie E M Kelly; Eileen M Denovan-Wright; Ganesh A Thakur
Journal:  ACS Chem Neurosci       Date:  2016-04-25       Impact factor: 4.418

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.  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

6.  3'-functionalized adamantyl cannabinoid receptor probes.

Authors:  Go Ogawa; Marcus A Tius; Han Zhou; Spyros P Nikas; Aneetha Halikhedkar; Srikrishnan Mallipeddi; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2015-03-20       Impact factor: 7.446

7.  Novel C-Ring-Hydroxy-Substituted Controlled Deactivation Cannabinergic Analogues.

Authors:  Shashank Kulkarni; Spyros P Nikas; Rishi Sharma; Shan Jiang; Carol A Paronis; Michael Z Leonard; Bin Zhang; Chandrashekhar Honrao; Srikrishnan Mallipeddi; Jimit Girish Raghav; Othman Benchama; Torbjörn U C Järbe; Jack Bergman; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2016-07-13       Impact factor: 7.446

8.  A high efficacy cannabinergic ligand (AM4054) used as a discriminative stimulus: Generalization to other adamantyl analogs and Δ(9)-THC in rats.

Authors:  Torbjörn U C Järbe; Brian J LeMay; Ganesh A Thakur; Alexandros Makriyannis
Journal:  Pharmacol Biochem Behav       Date:  2016-06-02       Impact factor: 3.533

9.  C3-heteroaroyl cannabinoids as photolabeling ligands for the CB2 cannabinoid receptor.

Authors:  Darryl D Dixon; Marcus A Tius; Ganesh A Thakur; Han Zhou; Anna L Bowman; Vidyanand G Shukla; Yan Peng; Alexandros Makriyannis
Journal:  Bioorg Med Chem Lett       Date:  2012-06-15       Impact factor: 2.823

10.  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
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