Hemisynthesis and preliminary evaluation of novel endocannabinoid analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 12, 2003, Pages 1977-1980

  El Fangour, Siham ^a   Balas, Laurence ^a   Rossi, Jean Claude ^a   Fedenyuk, Andrey ^b   Gretskaya, Natalia ^b   Bobrov, Mikhail ^b   Bezuglov, Vladimir ^b   Hillard, Cecilia J ^c   Durand, Thierry ^a  

^a CNRS   (France)

^b SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^c MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CANNABINOID 1 RECEPTOR; CANNABINOID DERIVATIVE; CARBENOID; ENDOCANNABINOID; ESTER; FATTY ACID AMIDASE; HYDROGEN; METHYL GROUP; OXOMETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0038440634     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00348-2     Document Type: Article

References (29)

1. Mechoulam R., Fride E., Marzo V.D. Eur. J. Pharmacol. 359:1998;1.
2. Devane W.A., Hanuš L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R. Science. 258:1992;1946.
3. (a) Mechoulam R., Ben-Shabat S., Hanus L., Ligumsky M., Kaminski N.E., Schatz A.R., Gopher A., Almog S., Martin B.R., Compton D.R., Pertwee R.G., Griffin G., Bayewitch M., Barg J., Vogel Z. Biochem. Pharmacol. 50:1995;83
4. (b) Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K. Biochem. Biophys. Res. Commun. 215:1995;89.
5. Porter A.C., Sauer J.M., Knierman M.D., Becker G.W., Berna M.J., Bao J., Nomikos G.G., Carter P., Bymaster F.P., Leese A.B., Felder C.C. J. Pharmacol. Exp. Ther. 301:2002;1020.
6. Hanuš L., Abus-Lafi S., Fride E., Breur A., Vogel Z., Shalev D.E., Kustanovich I., Mechoulam R. PNAS. 98:2001;3662.
7. Cravatt B.F., Prospero-Garcia O., Siuzdak G., Gilula N.B., Henriksen S.J., Boger D.L., Lerner R.A. Science. 268:1995;1506.
8. Huang S.M., Bisogno T., Petros T.J., Chang S.Y., Zavitsanos P.A., Zipkin R.E., Sivakumar R., Coop A., Maeda D.Y., De Petrocellis L., Burstein S., Di Marzo V., Walker J.M. J. Biol. Chem. 276:2001;42639.
9. Bezuglov V., Bobrov M., Gretskaya N., Gonchar A., Zinchenko G., Melck D., Bisogno T., Di Marzo V., Kuklev D., Rossi J.-C., Vidal J.-P., Durand T. Biomed. Chem. Lett. 11:2001;447.
10. Huang S.M., Bisogno T., Trevisani M., Al-Hayani A., De Petrocellis L., Fezza F., Tognetto M., Petros T.J., Krey J.F., Chu C.J., Miller J.D., Davies S.N., Geppetti P., Walker J.M., Di Marzo V. Proc. Natl. Acad. Sci. U.S.A. 99:2002;8400.
11. Mechoulam R., Panikashvili D., Shohami E. Trends in Molecular Medicine. 8:2002;58.
12. Goutopoulos A., Makriyannis A. Pharmacol. Ther. 95:2002;103.
13. Regio P.H. Prostaglandins Leukot. Essent. Fatty Acids. 66:2002;143.
14. Jarrahian A., Manna S., Edgemond W.S., Cambell W.B., Hillard C.J. J. Neurochem. 74:2000;2597.
15. Lopez-Rodriguez M.L., Viso A., Ortega-Gutierrez S., Lastres-Becker I., Gonzalez S., Fernandez-Ruiz J., Ramos J.A. J. Med. Chem. 44:2001;4505.
16. Khanolkar A.D., Makriyannis A. Life Sciences. 65:1999;607.
17. Van der Stelt M., Van Kuik J.A., Bari M., Van Zadelhoff G., Leeflang B.R., Veldink G.A., Finazzi-Agro A., Vliegenthart J.F., Maccarrone M. J. Med. Chem. 45:2002;3709.
18. Sugiura T., Kodaka T., Nakane S., Miyashita T., Kondo S., Suhara Y., Takayama H., Waku K., Seki C., Baba N., Ishima Y. J. Biol. Chem. 274:1999;2794.
19. Ng E.W., Aung M.M., Abood M.E., Martin B.R., Razdan R.K. J. Med. Chem. 42:1999;1975.
20. Suhara Y., Nakane S., Arai S., Takayama H., Waku K., Ishima Y., Sugiura T. Bioorg. Med. Chem. Lett. 11:2001;1985.
21. Berglund B.A., Boring D.L., Wilken G.H., Makriyannis A., Howlett A.C., Lin S. Prostaglandins Leukot. Essent. Fatty Acids. 59:1998;111.
22. Sugiura T., Kondo S., Sukagava A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K. Biochem. Biophys. Res. Commun. 512:1995;89.
23. Bezuglov V.V., Bobrov M.Yu., Gretskaya N.M., Archakov A.V., Serkov I.V., Fedenuyk A.P., Verevochkina E.Yu., Kogteva G.S., Titova O.Yu., Marvanov D.M., De Petrocellis L., Bisogno T., Di Marzo V., Manevich Y. Russian J. Bioorg. Chem. 24:1998;833.
24. Sheskin T., Hanuš L., Slager J., Vogel Z., Mechoulam R. J. Med. Chem. 40:1997;659.
25. 3, 150 MHz) δ (ppm): 14.1 (C20); 22.6 (C4); 23.0 (C19); 25.1 (2 α-Me); 25.5-25.6-27.2-29.3-31.5 (C3, C7, C10, C13, C16, C17, C18); 40.5 (C2); 61.5 (C2′); 66.1 (C1′); 127.5-127.9-128.2-128.3-128.6-129.5-130.5 (C5, C6, C8, C9, C11, C12, C14, C15); 178.2 (C1).
26. The yield of coupling with free ethyleneglycol never exceeded 65% regardless acyl fluoride or diisopropyl carbodiimide chemistry. Acylation of mono-hydroxyl compounds with 11 proceeded in 75% and above yields.
27. Tamaru Y., Ochiai H., Sanda F., Yoshida Z.-I. Tetrahedron Lett. 26:1985;5529.
28. 2-C); 29.6 (C15); 31.5 (C16); 39.5 (C3′); 42.9 (C2); 62.3 (C1′); 127.9 (C10 or C12); 128.0 (C12 or C10); 130.0 (C9 or C13); 130.2 (C13 or C9); 211.8 (C=O).
29. 2O).