Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 2, 2007, Pages 854-867

  Suhara, Yoshitomo ^a   Oka, Saori ^a   Kittaka, Atsushi ^a   Takayama, Hiroaki ^a   Waku, Keizo ^a   Sugiura, Takayuki ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 2 (HYDROXYMETHYL)TRICOSA 8,11,14,17 TETRAEN 4 ONE; 1,3 DIHYDROXYPROPAN 2 HENICOSA 6,9,12,15 TETRAENOATE; 1,3 DIHYDROXYPROPAN 2 YL ICOSA 8,11,14,17 TETRAENOATE; 1,3 DIHYDROXYPROPAN 2 YL NONA DECA 4,7,10,13 TETRAENOATE; 2 (HENICOSA 6,9,12,15 TETRAENYL)PROPANE 1,3 DIOL; 2 (HYDROXYMETHYL)TRICOSA 8,11,14,17 TETRAENE 1,4 DIOL; 2 ARACHIDONOYLGLYCEROL; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; ALKENE DERIVATIVE; ARACHIDONIC ACID; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; CARBENE; CARBON; HYDROXYL GROUP; KETONE DERIVATIVE; LIGAND;

ARTICLE; BIOLOGICAL ACTIVITY; CELL STRAIN HL 60; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME STRUCTURE; HUMAN; HUMAN CELL; ISOMER; PROTEIN EXPRESSION; RECEPTOR UPREGULATION;

ARACHIDONIC ACIDS; CELL LINE; GLYCERIDES; HL-60 CELLS; HUMANS; INDICATORS AND REAGENTS; LIGANDS; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; RECEPTORS, CANNABINOID; STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA;

EID: 33845285910     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.10.049     Document Type: Article

References (26)

1. Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., and Waku K. Biochem. Biophys. Res. Commun. 215 (1995) 89-97
2. Mechoulam R., Ben-Shabat S., Hanus L., Ligumsky M., Kaminski N.E., Schatz A.R., Gopher A., Almong S., Martin B.R., Compton D.R., Pertwee R.G., Griffin G., Bayewitch M., Barg J., and Vogel Z. Biochem. Pharmacol. 50 (1995) 83-90
3. Sugiura T., Kodaka T., Kondo S., Nakane S., Kondo H., Waku K., Ishima Y., Watanabe K., and Yamamoto I. J. Biochem. 122 (1997) 890-895
4. Sugiura T., Kodaka T., Nakane S., Miyashita T., Kondo S., Suhara Y., Takayama H., Waku K., Seki C., Baba N., and Ishima Y. J. Biol. Chem. 274 (1999) 2794-2801
5. Sugiura T., Kondo S., Kishimoto S., Miyashita T., Nakane S., Kodaka T., Suhara Y., Takayama H., and Waku K. J. Biol. Chem. 275 (2000) 605-612
6. Sugiura T., Kodaka T., Kondo S., Tonegawa T., Nakane S., Kishimoto S., Yamashita A., and Waku K. Biochem. Biophys. Res. Commun. 233 (1997) 207-210
7. Stella N., Schweitzer P., and Piomelli D. Nature 388 (1997) 773-778
8. Ameri A., and Simmet T. Naunyn Schmiedebergs Arch. Pharmacol. 361 (2000) 265-272
9. Lee M., Yang K.H., and Kaminski N.E. J. Pharmacol. Exp. Ther. 275 (1995) 529-536
10. Mechoulam R., Fride E., Ben-Shabat S., Meiri U., and Horowitz M. Eur. J. Pharmacol. 362 (1998) R1-R3
11. Jorda M.A., Verbakel S.E., Valk P.J., Vankan-Berkhoudt Y.V., Maccarrone M., Finazzi-Agro A., Lowenberg B., and Delwel R. Blood 99 (2002) 2786-2793
12. Walter L., Franklin A., Witting A., Wade C., Xie Y., Kunos G., Mackie K., and Stella N. J. Neurosci. 23 (2003) 1398-1405
13. Kishimoto S., Gokoh M., Oka S., Muramatsu M., Kajiwara T., Waku K., and Sugiura T. J. Biol. Chem. 278 (2003) 24469-24475
14. Sugiura T., and Waku K. Chem. Phys. Lipids 108 (2000) 89-106
15. Sugiura T., Kobayashi Y., Oka S., and Waku K. Prostaglandins Leukot. Essent. Fatty Acids 66 (2002) 173-192
16. Suhara Y., Takayama H., Nakane S., Miyashita T., Waku K., and Sugiura T. Chem. Pharm. Bull. 48 (2000) 903-907
17. Khanapure P.S., Shi X.-X., Powell S.W., and Rokach J. J. Org. Chem. 63 (1998) 337-427
18. Kerdesky A.J.F., Schmidt P.S., Holms H.J., Dyer D.R., Carter W.G., and Brooks W.D. J. Med. Chem. 30 (1987) 1177-1186
19. Parkkari T., Salo O.M., Huttunen K.M., Savinainen J.R., Laitinen J.T., Poso A., Nevalainen T., and Jarvinen T. Bioorg. Med. Chem. 14 (2006) 2850-2858
20. Bobrov M., Gretskaya N., Payet O., Bezuglov V., Durand T., Maurin L., Tourrel F., Adjali O., Rinaldi-Carmona M., and Muller A. Life Sci. 77 (2005) 1425-1440
21. Parkkari T., Myllymaki M., Savinainen J.R., Saario S.M., Castillo-Melendez J.A., Laitinen J.T., Nevalainen T., Koskinen A.M., and Jarvinen T. Bioorg. Med. Chem. Lett. 16 (2006) 2437-2440
22. Vandevoorde S., Saha B., Mahadevan A., Razdan R.K., Pertwee R.G., Martin B.R., and Fowler C.J. Biochem. Biophys. Res. Commun. 337 (2005) 104-109
23. Ghafouri N., Tiger G., Razdan R.K., Mahadevan A., Pertwee R.G., Martin B.R., and Fowler C.J. Br. J. Pharmacol. 143 (2004) 774-784
24. Hanus L., Abu-Lafi S., Fride E., Breuer A., Vogel Z., Shalev D.E., Kustanovich I., and Mechoulam R. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 3662-3665
25. Kishimoto S., Kobayashi Y., Oka S., Gokoh M., Waku K., and Sugiura T. J. Biochem. 135 (2004) 517-524
26. Brown J.M., Leppard S.J., Oakes J., and Thornthwaite D. Chirality 12 (2000) 496-504