Cannabinoids structure-activity relationships

Compton DR, Rice KC, De Costa BR, Razdan RK, Melvin LS, Johnson MR, and Martin BR (1993) Cannabinoid structure-activity relationships correlation of receptor binding and in vivo activities. J Pharmacol Exp... 

Most relevant for the affinity for A9-THC and analogs to CB-receptors are the phenolic hydroxyl group at C-1, the kind of substitution at C-9, and the properties of the side chain at C-3. Relating to the structure-activity relationships (SAR) between cannabinoids and the CB-receptors, many different modified strucfures of fhis subsfance group were developed and fesfed. The most important variations include variations of the side chain at the olivetolic moiety of the molecules and different substitutions at positions C-11 and C-9. One of the most popular analogous compounds of A9-THC is HU-210 or (-)-trans-ll-OH-A8-THC-DMH, a cannabinoid with a F,l-dimethylheptyl side... 

Makriyannis A, Banijamali A, Van der Schyf C, Jarrell H. The role of cannabinoid stereochemistry and absolute configuration and the orientation of A9-THC in the membrane bilayer. Structure-activity relationships of cannabinoids. In Rapaka RS, Makriyannis A, eds. Interactions of Cannabinoids with Membranes. National Institute on Drug Abuse Research Monograph 79. Rockville, MD US Department of Health and Human Services, 1987. 

Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, Pertwee R, Makriyannis A. Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 1999 42 769-776. 

For new information on the structure-activity relationships of cannabinoids see JMC 16,1200(1973), Arzneim, Forsch 22,1995... 

Much progress has recently been made in our understanding of structure-activity relationships of cannabinoids. In view of the current interest in the clinical usefulness of these compounds as analgesics, Chapter 5 gives a timely survey of present scientific knowledge of these drugs. 

Mechoulam, R., and Edery, H. Structure activity relationships in the cannabinoid series. In Mechoulam, R., ed. Marijuana Chemistry, Metabolism, Pharmacology and Clinical Effects. New York Academic Press, 1973. pp. 101-136. 

Rapaka, R.S. Makriyannis, A. Structure-Activity Relationships of the Cannabinoids Research Monograph 79 NIDA 1987 (ADM)87-1534 Randal, R.C. O Leary, A.M. Marijuana RX A Patients Fight for Medical Pot, 1998 ISBN 1-56025-166-2... 

The structure-activity relationships of dronabinol (32) on cannabinoid receptor activity have been investigated (see Table 15.14). Both the phenolic hydroxyl group and the C3 alkyl chain in (32) are critical for binding affinity. 

Gareau Y, Dufresne C, Gallant M, Rochette C, Sawyer N, Slipetz DM, Tremblay N, Weech PK, Metters KM, Labelle M (1996) Structure activity relationships of tetrahydrocannabinol analogues on human cannabinoid receptors. Bioorg Med Chem Lett 6 189-194... 

Ross RA, Gibson TM, Brockie HC, Leslie M, Pashmi G, Craib SJ, Di Marzo V, Pertwee RG (2001) Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens. Br J Pharmacol 132 631-640... 

Melvin LS, Johnson MR (1987) Structure-activity relationships of tricyclic and nonclassical bicyclic cannabinoids. NIDA Res Monogr 79 31-47... 

Melvin LS, Milne GM, Johnson MR, Subramaniam B, Wilken GH, Howlett AC (1993) Structure-activity relationships for cannabinoid receptor-binding and analgesic activity studies of bicyclic cannabinoid analogs. Mol Pharmacol 44 1008-1015... 

Sugiura T, Kodaka T, Nakane S, Miyashita T, Kondo S, Sahara Y, Takayama H, Waku K, Seki C, Baba N, Ishima Y (1999) Evidence that the cannabinoid CBI receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801... 

Eissenstat MA, Bell MR, D Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM, et al (1995) Aminoalkylindoles structure-activity relationships of novel cannabinoid mimetics. J Med Chem 38 3094-3105... 

Keywords Cannabinoid receptors Cannabinoid receptor probes Structure-activity relationships Selecrivity... 

Francisco MEY, Seltzman HH, Gilliam AF, Mitchell RA, Rider SL, Pertwee RG, Stevenson LA, Thomas BF (2002) Synthesis and structure-activity relationships of amide and hydrazide analogues of the cannabinoid CBl receptor antagonist N-(piperidi-nyl)-5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-lH-pyrazole-3-carboxamide (SR141716). J Med Chem 45 2708-2719... 

Katoch-Rouse R, Pavlova OA, Caulder T, Hoffman AF, Mukhin AG, Horti AG (2003) Synthesis, structure-activity relationship, and evaluation of SR141716 analogues development of central cannabinoid receptor ligands with lower lipophUicity. J Med Chem 46 642-645... 

Khanolkar AD, Makriyannis A (1999) Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci 65 607-616... 

Osgood PF, Howes JF, Razdan RK, Pars HG (1978) Drugs derived from cannabinoids. 7. Tachycardia and analgesia structure-activity relationships in 4 9-tetrahydrocannabinol and some synthetic analogues. J Med Chem 21 809-811... 

Razdan RK (1986) Structure-activity relationships in cannabinoids. Pharmacol Rev 38 75-149... 

Reggio PH (2002) Endocannabinoid structure-activity relationships for interaction at the cannabinoid receptors. Prostaglandins Leukot Essent Fatty Acids 66 143-160... 

Tarzia G, Duranti A, Tontini A, Spadoni G, Mor M, Rivara S, Vincenzo Plazzi P, Kathuria S, Piomelli D (2003) Synthesis and structure-activity relationships of a series of pyrrole cannabinoid receptor agonists. Bioorg Med Chem 11 3965-3973... 

Wiley JL, Compton DR, Dai D, Lainton JA, Phillips M, Huffman JW, Martin BR (1998) Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J Pharmacol Exp Ther 285 995-1004... 

---