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Literature DB >> 20621488

Synthesis and pharmacology of 1-methoxy analogs of CP-47,497.

John W Huffman¹, Seon A Hepburn, Patricia H Reggio, Dow P Hurst, Jenny L Wiley, Billy R Martin.

Abstract

Three 1-methoxy analogs of CP-47,497 (7, 8, and 19) have been synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors have been determined. Although these compounds exhibit selectivity for the CB(2) receptor none have significant affinity for either receptor. Modeling and receptor docking studies were carried out, which provide a rationalization for the weak affinities of these compounds for either receptor. Copyright (c) 2010 Elsevier Ltd. All rights reserved.

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Year: 2010 PMID： 20621488 PMCID： PMC2920039 DOI： 10.1016/j.bmc.2010.06.054

Source DB: PubMed Journal: Bioorg Med Chem ISSN： 0968-0896 Impact factor: 3.641

38 in total

1. CB2 cannabinoid receptor-mediated peripheral antinociception.

Authors: T P Malan; M M Ibrahim; H Deng; Q Liu; H P Mata; T Vanderah; F Porreca; A Makriyannis
Journal: Pain Date: 2001-09 Impact factor: 6.961

2. 1-Methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: new selective ligands for the CB2 receptor.

Authors: John W Huffman; Simon M Bushell; John R A Miller; Jenny L Wiley; Billy R Martin
Journal: Bioorg Med Chem Date: 2002-12 Impact factor: 3.641

3. Cannabinoid receptors CB1 and CB2: a characterization of expression and adenylate cyclase modulation within the immune system.

Authors: A R Schatz; M Lee; R B Condie; J T Pulaski; N E Kaminski
Journal: Toxicol Appl Pharmacol Date: 1997-02 Impact factor: 4.219

4. Molecular characterization of a peripheral receptor for cannabinoids.

Authors: S Munro; K L Thomas; M Abu-Shaar
Journal: Nature Date: 1993-09-02 Impact factor: 49.962

5. Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain.

Authors: Gerard M P Giblin; Celestine T O'Shaughnessy; Alan Naylor; William L Mitchell; Andrew J Eatherton; Brian P Slingsby; D Anthony Rawlings; Paul Goldsmith; Andrew J Brown; Carl P Haslam; Nick M Clayton; Alex W Wilson; Iain P Chessell; Andrew R Wittington; Richard Green
Journal: J Med Chem Date: 2007-05-04 Impact factor: 7.446

Synthesis and pharmacology of 1-methoxy analogs of CP-47,497.

1. CB2 cannabinoid receptor-mediated peripheral antinociception.

2. 1-Methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: new selective ligands for the CB2 receptor.

3. Cannabinoid receptors CB1 and CB2: a characterization of expression and adenylate cyclase modulation within the immune system.

4. Molecular characterization of a peripheral receptor for cannabinoids.

5. Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain.

6. Paradoxical pharmacological effects of deoxy-tetrahydrocannabinol analogs lacking high CB1 receptor affinity.

7. Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol.

8. Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities.

9. Induction of CB2 receptor expression in the rat spinal cord of neuropathic but not inflammatory chronic pain models.

10. Cannabinoid receptor localization in brain.

1. Effects of acute and repeated dosing of the synthetic cannabinoid CP55,940 on intracranial self-stimulation in mice.