Potent anandamide analogs: The effect of changing the length and branching of the end pentyl chain

Journal of Medicinal Chemistry

Volumn 40, Issue 22, 1997, Pages 3617-3625

  Ryan, William J ^a   Kenneth Banner, W ^a   Wiley, Jenny L ^a,b   Martin, Billy R ^a,b   Razdan, Raj K ^a  

^a ORGANIX INC   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANANDAMIDE;

AMINO ACID SUBSTITUTION; ANALGESIA; ARTICLE; DRUG EFFECT; DRUG POTENCY; HYDROLYSIS; METABOLIC REGULATION; MOLECULAR MODEL; NONHUMAN; RECEPTOR AFFINITY; REPRODUCIBILITY;

ANIMALS; ARACHIDONIC ACIDS; BEHAVIOR, ANIMAL; CANNABINOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICE; MOLECULAR STRUCTURE; POLYUNSATURATED ALKAMIDES; RADIOLIGAND ASSAY; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9844228519     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970212f     Document Type: Article

References (33)

1. Devane, W. A.; Hannus, L.; Breuer, A.; Pertwee, R. G.; Stevenson, L. A.; Griffin, G.; Gibson, D.; Mandelbaum, A.; Etinger, A.; Mechoulam, R. Isolation and Structure of a Brain Constituent that Binds to the Cannabinoid Receptor. Science 1992, 258, 1946-1949.
2. Fride, E.; Mechoulam, R. Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent. Eur. J. Pharmacol. 1993, 231, 313-314.
3. Felder, C. C.; Briley, E. M.; Axelrod, J.; Simpson, J. T.; Mackie, K.; Devane, W. A. Anandamide, an Endogenous Cannabimimetic Eicosanoid, Binds to the Cloned Human Cannabinoid Receptor and Stimulates Receptor-mediated Signal Transduction. Proc. Natl. Acad. Sci. 1993, 90, 7656-7660.
4. Vogel, Z.; Barg, J.; Levy, R.; Saya, D.; Heldman, E.; Mechoulam, R. Anandamide, a brain endogenous compound, interacts specifically with cannabinoid receptors and inhibits adenylate cyclase. J. Neurochem. 1993, 61, 352-355.
5. Mechoulam, R.; Hanus, L.; Martin, B. R. Search for endogenous ligands of the cannabinoid receptor. Biochem. Pharm. 1994, 48, 1537-1544.
6. Smith, P. B.; Compton, D. R.; Welch, S. P.; Razdan, R. K.; Mechoulam, R.; Martin, B. R. The Pharmacological Activity of Anandamide, a Putative Endogenous Cannabinoid, in Mice. J. Pharmacol. Exp. Ther. 1994, 270, 219-227.
7. Pinto, J. C.; Potie, F.; Rice, K. C.; Boring, D.; Johnson, M. R.; Evans, D. M.; Wilken, G.; Cantrell, C. H.; Howlett, A. C. Cannabinoid Receptor Binding and Agonist Activity of Amides and Esters of Arachidonic Acid. Mol. Pharmacol. 1994, 46, 516-522.
8. Abadji, V.; Lin, S.; Taha, G.; Griffin, G.; Stevenson, L. A.; Pertwee, R. G.; Makriyannis, A. (R)-Methanandamide: A Chiral Novel Anandamide Possessing Higher Potency and Metabolic Stability. J. Med. Chem. 1994, 37, 1889-1893.
9. Adams, I.; Ryan, W.; Singer, M.; Razdan, R. K.; Compton, D. R.; Martin, B. R. Pharmacological and Behavioral Evaluation of Alkylated Anandamide Analogs. Life Sci. 1995, 56, 2041-2048.
10. Adams, I. B.; Ryan, W.; Singer, M.; Thomas, B. F.; Compton, D. R.; Razdan, R. K.; Martin, B. R. Evaluation of Cannabinoid Receptor binding and in vivo Activities of Anandamide Analogs. J. Pharmacol. Exp. Ther. 1995, 273, 1172-1181.
11. (a) Khanolkar, A. D.; Abadji, V.; Lin, S.; Hill, W. A. G.; Taha, G.; Abouzid, K.; Meng, Z.; Fan, P.; Makriyannis, A. Head Group Analogs of Arachidonylethanolamide, the Endogenous Cannabinoid Ligand. J. Med. Chem. 1996, 39, 4515-4519.
12. (b) Sheskin, T.; Hanus, L.; Shager, J.; Vogel, J.; Mechoulam, R. Structural Requirements for Binding of Anandamide-Type Compounds to the Brain Cannabinoid Receptor. J. Med. Chem. 1997, 40, 659-667
13. Deutsch, D. G.; Chin, S. A. Enzymatic Synthesis and Degradation of Anandamide, A Cannabinoid Receptor Agonist. Biochem. Pharm. 1993, 46, 791-796.
14. Childers, S. R.; Sexton, T.; Roy, M. B. Effects of anandamide on cannabinoid receptors in rat brain membranes. Biochem. Pharmacol. 1994, 47, 711-715.
15. Hanus, L.; Gopher, A.; Almog, S.; Mechoulam, R. Two New Unsaturated Fatty Acid Ethanolamides in Brain that Bind to the Cannabinoid Receptor. J. Med. Chem. 1993, 36, 3032-3034.
16. Thomas, B. F.; Adams, I. B.; Mascarella, S. W.; Martin, B. R.; Razdan, R. K. Structure-Activity Analysis of Anandamide Analogs: Relationship to a Cannabinoid Pharmacophore. J. Med. Chem. 1996, 39, 471-479.
17. Razdan, R. K. Structure-Activity Relationships in Cannabinoids. Pharmacol. Rev. 1986, 38, 21-43.
18. Corey, E. J.; Iguchi, S.; Albright, J. O.; De, B. Studies on the Conformational Mobility of Arachidonic Acid. Facile Macrolactonization of 20-Hydroxyarachidonic Acid. Tetrahedron Lett. 1983, 24, 37-40.
19. Manna, S.; Falck, J. R.; Chacos, N.; Capdevila, J. Synthesis of Arachidonic Acid Metabolites Produced by Purified Kidney Cortex Microsomal Cytochrome P-450. Tetrahedron Lett. 1983, 24, 33-36.
20. Corey, E. J.; Niwa, H.; Falck, J. R. Selective Epoxidation of Eicosa-cis-5,8,11,14-tetraenoic (Arachidonic) Acid and Eicosa-cis-8,11,14-trienoic Acid. J. Am. Chem. Soc. 1979, 101, 1586-1587.
21. Perrier, H.; Prasit, P.; Wang, Z. Synthesis of a Radioactive Photoaffinity Arachidonic Acid Analog. Tetrahedron Lett. 1994, 35, 1501-1502.
22. McDonald, R. N.; Campbell, T. W. 1,4-Diphenyl-1,3-Butadiene. Organic Syntheses; Wiley: New York, 1973; Coll. Vol. 5, pp 499-501.
23. Labelle, M.; Falgueyret, J. P.; Riendeau, D.; Rokach, J. Synthesis of Two Analogues of Arachidonic Acid and their Reactions with 12-Lipoxygenase. Tetrahedron 1990, 46, 6301-6310.
24. Munch-Petersen, J. 3-Methylheptanoic Acid. Organic Syntheses; Wiley: New York, 1973; Coll. Vol. 5, pp 762-766.
25. Cahiez, G.; Alami, M. Copper-Catalyzed Conjugate Addition of Organomagnesium Reagents to α,β-Ethylenic Esters: A Simple high yield Procedure. Tetrahedron Lett. 1990, 31, 7425-7428.
26. Grassland, R. K.; Servis, K. L. A Facile Synthesis of Methanesulfonate Esters. J. Org. Chem. 1970, 35, 3195-3196.
27. Corey, E. J.; Suggs, J. W. Pyridinium Chlorochroinate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett. 1975, 2647-2650.
28. 9-THC: Reassesment of the Putative Three Point Cannabinoid-Receptor Interaction. Drug Alcohol Depend. 1995, 37, 231-240.
29. Dewey, W. L.; Harris, L. S.; Howews, J. F.; Nuite, J. A. The effect of various neurohumoral modulators on the activity of morphine and the narcotic antagonists in the tail-flick and phenylquinone tests. J. Pharmacol. Exp. Ther. 1970, 175, 435-442.
30. Pertwee, R. G. The ring test: A quantitative method for assessing the cataleptic effect of cannabis in mice. Br. J. Pharmacol. 1972, 46, 753-763.
31. 50) on an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
32. DeLean, A.; Munson, P. J.; Rodbard, D. Simultaneous analysis of families of sigmoidal curves: Application to bioassay, radio-ligand assay, and physiological dose-response curves. Am. J. Physiol. 1978, 235, E97-E102.
33. Compton, D. R.; Johnson, M. R.; Melvin, L. S.; Martin, B. R. Pharmacological profile of a series of bicyclic cannabinoid analogs: Classification as cannabimimetic agents. J. Pharmacol. Exp. Ther. 1992, 260, 201-209.