Unique analogues of anandamide: Arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas

Journal of Medicinal Chemistry

Volumn 42, Issue 11, 1999, Pages 1975-1981

  Ng, Edward W ^a   Aung, Mie Mie ^b   Abood, Mary E ^b   Martin, Billy R ^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

1 NORARACHIDONYL 3 (2' FLUOROETHYL)UREA; 1 NORARACHIDONYL 3 (2' HYDROXYETHYL)UREA; 1 NORARACHIDONYL 3 METHYLUREA; ANANDAMIDE; ARACHIDONIC ACID DERIVATIVE; CANNABINOID RECEPTOR AGONIST; CARBAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CATALEPSY; CHEMICAL BOND; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING SITE; DRUG DEGRADATION; DRUG HYDROLYSIS; DRUG POTENCY; DRUG SYNTHESIS; HEATING; HYPOTHERMIA; MOUSE; NONHUMAN; REACTION ANALYSIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANALGESICS, NON-NARCOTIC; ANIMALS; ARACHIDONIC ACIDS; BODY TEMPERATURE; CANNABINOIDS; CARBAMATES; HYDROLYSIS; LIGANDS; MICE; MOTOR ACTIVITY; POLYUNSATURATED ALKAMIDES; RADIOLIGAND ASSAY; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP; UREA;

EID: 0345593493     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980711w     Document Type: Article

References (33)

1. Devane, W. A.; Hanus, 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, 237, 313-314.
3. 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.
4. Crowley, J. N.; Corwin, R. L.; Robinson, J. K.; Felder, C. C.; Devane, W. A.; Axelrod, J. Anandamide, an endogenous ligand of the cannabinoid receptor, induces hypomobility and hypothermia in vivo in rodents. Pharmacol. Biochem. Behav. 1993, 46, 967-972.
5. 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.
6. Howlett, A. C.; Qualy, J. M.; Khachaturian, L. L. Involvement of Gi in the inhibition of adenylate cyclase by marihuana. Neuropharmacology 1987, 26, 507.
7. Mackie, K.; Devane, W. A,; Hille, B. Anandamide, an Endogenous Cannabinoid, Inhibits Calcium Currents as a Partial Agonist in N18 Neuroblastoma Cells. Mol. Pharmacol. 1993, 44, 498-503.
8. Howlett, A. C.; Champion-Doron, T. M.; McMahon, L. L.; Westlake, T. M. The cannabinoid receptor: biochemical and cellular properties on neuroblastoma cells. Pharmacol. Biochem. Behav. 1991, 40, 565.
9. Deutsch, D. G.; Chin, S. A. Enzymatic Synthesis and Degradation of Anandamide. Biochem. Pharmacol. 1993, 46, 791-796.
10. Guilders, S. R.; Sexton, T.; Roy, M. B. Effects of anandamide on cannabinoid receptors in rat brain membranes. Biochem. Pharmacol. 1994, 47, 711-715.
11. Mechoulam, R.; Hanus, L.; Martin, B. R. Search for endogenous ligands of the cannabinoid receptor. Biochem. Pharmacol. 1994, 48, 1537-1544.
12. 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 Analogues. J. Pharmacol. Exp. Ther. 1995, 273, 1172-1181.
13. Pinto, J. C.; Potie, F.; Rice, K. C.; Boring, D.; Johnson, M. R.; Evans, D. M.; Wilken, G. H.; 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.
14. Sheskin, T.; Hanus, L.; Slager, J.; Vogel, Z.; Mechoulam, R. Structural Requirements for Binding of Anandamide-Type Compounds to the Brain Cannabinoid Receptor. J. Med. Chem. 1997, 40, 659-667.
15. Khanolkar, A. D.; Abadji, V.; Lin, S.; Hill, W. A. G.; Taha, G.; Abouzid, K.; Meng, Z.; Fan, P.; Makriyannis, A. Headgroup Analogues of Arachidonylethanolamide, the Endogenous Cannabinoid Ligand. J. Med. Chem. 1996, 39, 4515-4519.
16. 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.
17. Thomas, B. F.; Adams, I. B.; Mascarella, S. W.; Martin, B. R.; Razdan, R. K. Structure - Activity Analysis of Anandamide Analogues: Relationship to a Cannabinoid Pharmacophore. J. Med. Chem. 1996, 39, 471-479.
18. Adams, I. B.; Ryan, W.; Singer, M.; Razdan, R. K.; Compton, D. R.; Martin, B. R. Pharmacological and Behavioral Evaluation of Alkylated Anandamide Analogues. Life Sci. 1995, 56, 2041-2048.
19. Wiley, J. L,; Golden, K. M.; Ryan, W. J.; Balster, R. L.; Razdan, R. K.; Martin, B. R. Evaluation of Cannabimimetic Discriminative Stimulus Effects of Anandamide and Methylated Fluoroanandamide in Rhesus Monkeys. Pharmacol. Biochem. Behav. 1997, 58, 1139-1143.
20. Ryan, W. J.; Banner, W. K.; Crocker, P. J.; Martin, B. R.; Razdan, R. K Synthesis of (+)-and (-)-2-Methylarachidonyl-2′-Fluoroethylamide (0-689). Bioorg. Med. Chem. Lett. 1997, 7, 2669-2672.
21. Freedman, H. H.; Dubois, R. A. An Improved Williamson Ether Synthesis Using Phase Transfer Catalysis. Tetrahedron Lett. 1975, 38, 3251-3254.
22. Shioiri, T.; Ninomiya, K.; Yamada, S. Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis. J. Am. Chem. Soc. 1972, 94, 6203-6205.
23. Ninomiya, K.; Shioiri, T.; Yamada, S. Phosphorus in Organic Synthesis-VII. Diphenyl Phosphorazidate (DPPA). A New Convenient Reagent for a Modified Curtius Reaction. Tetrahedron 1994, 30, 2151-2157.
24. Morgan, A. B.; Gainor, J. A. Chapter 26. Approaches to the Discovery of Non-Peptide Ligands for Peptide Receptors and Peptidases. In Annual Reports in Medicinal Chemistry; Alden, R. C., Ed.; Academic Press: San Diego, CA, 1989; pp 243-252.
25. 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.
26. Barg, J.; Fride, E.; Hanus, L.; Levy, R.; Matus-Leibovitch, N.; Heldman, E.; Bayewitch, M.; Mechoulam, R.; Vogel, Z. Cannabinomimetic behavioral effects of and adenylate cyclase inhibition by two new endogenous anandamides. Eur. J. Pharmacol. 1995, 257, 145-152.
27. Ryan, W. J.; Banner, W. K.; Wiley, J. L.; Martin, B. R.; Razdan, R. K. Potent Anandamide Analogues: The Effect of Changing the Length and Branching of the End Pentyl Chain. J. Med. Chem. 1997, 40, 3617-3625.
28. Seltzman, H. H.; Fleming, D. N.; Thomas, B. F.; Gilliam, A. F.; McCallion, D. S.; Pertwee, R. G.; Compton, D. R.; Martin, B. R. Synthesis and Pharmacological Comparison of Dimethylheptyl and Pentyl Analogues of Anandamide. J. Med. Chem. 1997, 40, 3626-3634.
29. Showalter, V. M.; Compton, D. R.; Martin, B. R.; Abood, M. E. Evaluation of binding in a transfected cell line expressing a peripheral Cannabinoid receptor (CB2): Identification of cannabinoid receptor subtype selective ligands. J. Pharmacol. Exp. Ther. 1896, 278, 989-999.
30. Dewey, W. L.; Harris, L. S.; Howews, J. F.; Nuite, J. A. The effect of various neurohumoral mudulators on the activity of morphine and the narcotic antagonists in the tail-flick and phenylquinone tests. J. Pharmacol. Exp. Ther. 1970, 775, 435-442.
31. 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.
32. 50) on an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
33. 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.