Oxaza adamantyl cannabinoids. A new class of cannabinoid receptor probes

Journal of Organic Chemistry

Volumn 71, Issue 20, 2006, Pages 7800-7804

  Le Goanvic, David ^a   Tius, Marcus A ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; NITROGEN COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AROMATIC RINGS; CANNABINOID RECEPTOR PROBES; TRICYCLIC CANNABINOIDS;

METABOLITES;

ADAMANTANE DERIVATIVE; AROMATIC COMPOUND; BENZENE DERIVATIVE; BENZYNE DERIVATIVE; BROMONONAFLATE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID DERIVATIVE; CANNABINOID RECEPTOR; PHLOROGLUCINOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ADAMANTANE; ANIMALS; CANNABINOIDS; LIGANDS; MOLECULAR PROBES; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; RECEPTORS, CANNABINOID;

EID: 33749118900     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061352c     Document Type: Article

References (45)

1. Devane, W. A.; Dysarz, F. A., III.; Johnson, M. R.; Melvin, L. S.; Howlett, A. C. Mol. Pharmacol. 1988, 34, 605-613.
2. Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. l. Nature (London) 1990, 346, 561-564.
3. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Nature (London) 1993, 365, 61-65.
4. For leading references, see: (a) Huffman, J. W.; Miller, J. R. A.; Liddle, J.; Yu, S.; Thomas, B. F.; Wiley, J. L.; Martin, B. R. Bioorg. Med. Chem. 2003, 11, 1397-1410.
5. (b) Papahatjis, D. P.; Nikas, S. P.; Kourouli, T.; Chari, R.; Xu, W.; Pertwee, R. G.; Makriyannis, A. J. Med. Chem. 2003, 46, 3221-3229.
6. (c) Papahatjis, D. P.; Nikas, S. P.; Andreou, T.; Makriyannis, A. Bioorg. Med. Chem. Lett. 2002, 12, 3583-3586.
7. (d) Khanolkar, A. D.; Lu, D.; Fan, P.; Tian, X.; Makriyannis, A. Bioorg. Med. Chem. Lett. 1999, 9, 2119-2124.
8. (e) Huffman, J. W.; Liddle, J.; Duncan, S. G., Jr.; Yu, S.; Martin, B. R.; Wiley, J. L. Bioorg. Med. Chem. 1998, 6, 2383-2396.
9. (f) Papahatjis, D. P.; Kourouli, T.; Abadji, V.; Goutopoulos, A.; Makriyannis, A. J. Med. Chem. 1998, 41, 1195-1200.
10. (g) Busch-Petersen, J.; Hill, W. A.; Fan, P.; Khanolkar, A.; Xie, X.-Q.; Tius, M. A.; Makriyannis, A. J. Med. Chem. 1996, 39, 3790-3796.
11. (a) Roesch, S.; Ramer, R.; Brune, K.; Hinz, B. J. Pharm. Exp. Ther. 2006, 316, 1219-1228.
12. (b) Jarvinen, T.; Pate, D. W.; Laine, K. Pharmacol. Ther. 2002, 95, 203-220.
13. (a) Huang, S. M.; Walker, J. M. In Cannabinoids as Therapeutics; Mechoulam, R., Ed.; Birkhäuser Verlag: Basel, 2005; p 149.
14. (b) Smith, P. F. Curr. Opin. Invest. Drugs 2002, 3, 859-864.
15. (a) Barth, F.; Rinaldi-Carmona, M. In Cannabinoids as Therapeutics; Mechoulam, R., Ed.; Birkhäuser Verlag: Basel, 2005; p 219.
16. (b) Koch, J. E. Pharmacol., Biochem. Behav. 2001, 68, 539-543.
17. (a) Adams, R. Harvey Lect. 1942, 37, 168-197.
18. (b) Adams, R.; Harfenist, M.; Loewe, S. J. Am. Chem. Soc. 1949, 71, 1624-1628.
19. Lu, D.; Meng, Z.; Thakur, G. A.; Fan, P.; Steed, J.; Tartal, C. L.; Hurst, D. P.; Reggio, P. H.; Deschamps, J. R.; Parrish, D. A.; George, C.; Järbe, T. U. C.; Lamb, R. J.; Makriyannis, A. J. Med. Chem. 2005, 48, 4576-4585.
20. See also: (a) McLaughlin, P. J.; Lu, D.; Winston, K. M.; Thakur, G.; Swezey, A.; Makriyannis, A.; Salamone, J. D. Pharmacol., Biochem. Behav. 2005, 81, 78-88.
21. (b) Järbe, T. U. C.; DiPatrizio, N. V.; Lu, D.; Makriyannis, A. Behav. Pharmacol. 2004, 15, 517-521.
22. (a) Stetter, H.; Heckel, K. Tetrahedron Lett. 1972, 9, 801-804.
23. (b) Stetter, H.; Heckel, K. Chem. Ber. 1973, 106, 339-348.
24. (a) Portmann, R. E.; Ganter, C. Helv. Chem. Acta 1973, 56, 1962-1985.
25. (b) Ganter, C.; Portmann, R. E. Helv. Chem. Acta 1971, 54, 2069-2077.
26. Archer, R. A.; Blanchard, W. B.; Day, W. A.; Johnson, D. W.; Lavagnino, E. R.; Ryan, C. W.; Baldwin, J. E. J. Org. Chem. 1977, 42, 2277-2284.
27. See: Boger, D. L.; Mullican, M. D.; Hellberg, M. R.; Patel, M. J. Org. Chem. 1985, 50, 1904-1911.
28. 2S is used as the reducing agent, as was the case in the laboratory that reported the accident in 1990. We routinely use thiourea for ozonide decomposition and have experienced no problems with this reaction. The use of thiourea for ozonolysis workups has been described: Gupta, D.; Soman, R.; Dev, S. Tetrahedron 1982, 38, 3013-3018.
29. Drake, D. J.; Jensen, R. S.; Busch-Petersen, J.; Kawakami, J. K.; Conception Fernandez-Garcia, M.; Fan, P.; Makriyannis, A.; Tius, M. A. J. Med. Chem. 1998, 41, 3596-3608.
30. Zhang, X.; Sui, Z. Tetrahedron Lett. 2003, 44, 3071-3073.
31. Neuville, L.; Bigot, A.; Tran Huu Dau, M. E.; Zhu, J. J. Org. Chem. 1999, 64, 7638-7642.
32. Buchwald has reported palladium-catalyzed aminations of aryl nonaflates: Anderson, K. W.; Mendez-Perez, M.; Priego, J.; Buchwald, S. J. Org. Chem. 2003, 68, 9563-9573.
33. (a) Hamura, T.; Hosoya, T.; Yamaguchi, H.; Kuriyama, Y.; Tanabe, M.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Helv. Chim. Acta 2002, 85, 3589-3604.
34. (b) Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 3534-3535.
35. (c) Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 2, 177-179.
36. For related work, see: Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198-3209.
37. Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377-3380.
38. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 3090-3100.
39. Hanessian, S.; Delorme, D.; Dufresne, Y. Tetrahedron Lett. 1984, 25, 2515-2518.
40. For an example of the application of this method to a polyfunctional molecule, see: Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685.
41. Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc., Perkin Trans. 1 1997, 9, 1307-1313.
42. Marchand, A. P.; Kumar, V. S.; Hariprakasha, H. K. J. Org. Chem. 2001, 66, 2072-2077.
43. In recent work, we have determined that the yield of the reductive cleavage step can be improved greatly by limiting the amount of water that is used during workup, thereby minimizing losses of product.
44. For a review of cannabinoid synthesis, see: Tius, M. A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1997; Vol. 19, p 185.
45. For an alternative approach to the synthesis of C3 amino cannabinoids, see: Petrzilka, T.; Lusuardi, W. G. Helv. Chim. Acta 1973, 56, 510-518.