Unsaturated side chain β-11-hydroxyhexahydrocannabinol analogs

Journal of Medicinal Chemistry

Volumn 39, Issue 19, 1996, Pages 3790-3796

  Busch Petersen, Jakob ^a   Hill, W Adam ^b   Fan, Pusheng ^b   Khanolkar, Atmaram ^b   Xie, Xuang Qun ^b   Tius, Marcus A ^a   Makriyannis, Alexandros ^b  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CANNABINOID RECEPTOR; CANNABINOL DERIVATIVE;

ANIMAL CELL; ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FOREBRAIN; MOLECULAR MODEL; MOUSE; NONHUMAN; RAT; SPLEEN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNAPTOSOME;

ANIMALS; CANNABINOIDS; CELL MEMBRANE; COMPUTER SIMULATION; MICE; MODELS, MOLECULAR; PROSENCEPHALON; RATS; RECEPTOR, CANNABINOID, CB2; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP; SYNAPTOSOMES; TETRAHYDROCANNABINOL;

EID: 0029795878     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950934b     Document Type: Article

References (28)

1. Razdan, R. K. Structure-Activity Relationships in Cannabinoids. Pharmacol. Rev. 1986, 38, 75-149.
2. Makriyannis, A.; Rapaka, R. S. The Molecular Basis of Cannabinoid Activity. Life Sci. 1990, 47, 2173-2184.
3. Adams, R. Marijuana. Harvey Lectures 1942, 37, 168-197.
4. 8-Tetrahydrocannabinol with Potent Biological Activity. J. Med. Chem. 1976, 19, 1328-1330. (c) Loev, B.; Bender, P. E.; Dowalo, F.; Macko, E.; Fowler, P. J. Cannabinoids. Structure-Activity Studies Related to 1,2-Dimethylheptyl Derivatives. J. Med. Chem. 1973, 16, 1200-1206.
5. 8-Tetrahydrocannabinol with Potent Biological Activity. J. Med. Chem. 1976, 19, 1328-1330. (c) Loev, B.; Bender, P. E.; Dowalo, F.; Macko, E.; Fowler, P. J. Cannabinoids. Structure-Activity Studies Related to 1,2-Dimethylheptyl Derivatives. J. Med. Chem. 1973, 16, 1200-1206.
6. 8-Tetrahydrocannabinol with Potent Biological Activity. J. Med. Chem. 1976, 19, 1328-1330. (c) Loev, B.; Bender, P. E.; Dowalo, F.; Macko, E.; Fowler, P. J. Cannabinoids. Structure-Activity Studies Related to 1,2-Dimethylheptyl Derivatives. J. Med. Chem. 1973, 16, 1200-1206.
7. Archer, R. A.; Blanchard, W. B.; Day, W. A.; Johnson, D. W.; Lavagnino, E. R.; Ryan, C. W.; Baldwin, J. E. Cannabinoids. 3. Synthetic Approaches to 9-Ketocannabinoids. Total Synthesis of Nabilone. J. Org. Chem. 1977, 42, 2277-2284.
8. 8-tetrahydrocannabinol-9-carboxylic Acid Methyl Ester. J. Org. Chem. 1990, 55, 5711-5714.
9. Rubottom, G. M.; Kim, C. Preparation of Methyl Ketones by the Sequential Treatment of Carboxylic Acids with Methyllithium and Chlorotrimethylsilane. J. Org. Chem. 1983, 48, 1550-1552.
10. Negishi, E.; King, A. O.; Klima, W. L.; Patterson, W.; Silveira, A., Jr. Conversion of Methylketones Into Terminal Acetylenes and (E)-Trisubstituted Olefins of Terpenoid Origin. J. Org. Chem. 1980, 45, 2526-2528.
11. Chong, J. M.; Wong, S. Alkylation of Stabilized Acetylides in DMSO. Preparation of α,β-Acetylenic Alcohols and Acetals. Tetrahedron Lett. 1986, 27, 5445-5448.
12. Lipshutz, B. H.; Fatheree, P.; Hagen, W.; Stevens, K. L. Higher Order, Mixed Cyanocuprates Derived From n-Lithioimidazole and Pyrrole: New "Dummy" Ligand Alternatives in Organocopper Chemistry. Tetrahedron Lett. 1992, 33, 1041-1044.
13. Conia, J.-M.; Limasset, J.-C. L'utilisation du t-Amylate de Sodium Dans les Réactions de Wittig. Bull. Soc. Chim. Fr. 1967, 6, 1936-1938.
14. Corey, E. J.; Tius, M. A. 1-Diphenylphosphonio-1-methoxymethyllithium, a Useful Reagent For the Synthesis of Aldehydes From Hindered Ketones. Tetrahedron Lett. 1980, 21, 3535-3538.
15. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Silicon in Synthesis 17. Chloromethyl(trimethylsilyl)lithium - a New Reagent For the Direct Conversion of Aldehydes and Ketones Into α,β-Epoxytrimethylsilanes. Tetrahedron 1983, 39, 867-876.
16. Hecker, S. J.; Heathcock, C. H. Total Synthesis of (+)-Dihydromevinolin. J. Am. Chem. Soc. 1986, 108, 4586-4594.
17. Lindlar, H.; Dubuis, R. Palladium Catalyst for Partial Reduction of Acetylenes. Org. Synth. 1966, 46, 89-92; Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 880.
18. Lindlar, H.; Dubuis, R. Palladium Catalyst for Partial Reduction of Acetylenes. Org. Synth. 1966, 46, 89-92; Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 880.
19. 2o. J. Org. Chem. 1987, 52, 2958-2960.
20. (b) Schwarz, M.; Graminski, G. F.; Waters, R. M. Insect Sex Pheromones. Stereospecific Synthesis of (E)-13, 13-Dimethyl-11-Tetradecen-1-ol Acetate Via a Thiophenol-Mediated Olefin Inversion. J. Org. Chem. 1986, 51, 260-263.
21. Dodd, P. R.; Hardy, J. A.; Oakley, A. E.; Edwardson, J. A.; Perry, E. K.; Delaunoy, J.-P. A Rapid Method for Preparing Synaptosomes: Comparison, With Alternative Procedures. Brain Res. 1981, 226, 107-118.
22. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3102.
23. Johnson, M. R.; Melvin, L. S. In Cannabinoids as Therapeutic Agents; Mechoulam, R., Ed.; CRC Press: Boca Raton, FL, 1986.
24. 9-Tetrahydrocannabinolic Acid B. Acta Chem. Scand. 1975, B29, 379-384.
25. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular Characterization of a Peripheral Receptor for Cannabinoids. Nature 1993, 365, 61-65.
26. Hill, W. A. G.; Morse, K. L.; Makriyannis, A. Unpublished results.
27. Kaminski, N. E.; Abood, M. E.; Kessler, F. K.; Martin, W. R.; Schatz, A. R. Identification of a Functionally Relevant Cannabinoid Receptor on Mouse Spleen Cells that IS Involved in Cannabinoid-Mediated Immune Modulation. Mol. Pharmacol. 1992, 42, 736-742.
28. Xie, X. Q.; Yang, D. P.; Melvin, L. S.; Makriyannis, A. Conformational Analysis of the Prototype Nonclassical Cannabinoid CP-47,497, Using 2D NMR and Computer Molecular Modeling. J. Med. Chem. 1994, 37, 1418-1426.