Synthesis and pharmacological evaluation of sulfamide-based analogues of anandamide

European Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2009, Pages 4889-4895

  Cano, Carolina ^a   Páez, Juan Antonio ^a   Goya, Pilar ^a   Serrano, Antonia ^b   Pavón, Javier ^b   Rodríguez de Fonseca, Fernando ^b   Suardíaz, Margarita ^c   Martín, María Isabel ^c  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b HOSPITAL REGIONAL UNIVERSITARIO DE MÁLAGA   (Spain)

^c UNIVERSIDAD REY JUAN CARLOS   (Spain)

Author keywords

Anandamide; Arachidonyl; Cannabinoid; FAAH; Sulfamide

Indexed keywords

ANANDAMIDE; ARACHIDONYL SULFAMIDE DERIVATIVE; CANNABINOID 1 RECEPTOR; FATTY ACID AMIDASE; LINOLEYL SULFAMIDE DERIVATIVE; PROPANE; SULFAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING ASSAY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; LIPOPHILICITY; MALE; MOUSE; NONHUMAN;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; CELLS, CULTURED; ENDOCANNABINOIDS; ENZYME INHIBITORS; MALE; MOLECULAR STRUCTURE; POLYUNSATURATED ALKAMIDES; RATS; SULFONAMIDES; VAS DEFERENS;

EID: 70449642441     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.08.003     Document Type: Article

References (26)

1. Lambert D.M., and Fowler C.J. J. Med. Chem. 48 (2005) 5059-5087
2. Hanus L.O. Med. Res. Rev. (2008) 1-59
3. Howlett A.C., Barth F., Bonner T.I., Cabral G., Casellas P., Devane W.A., Felder C.C., Herkenham M., Mackie K., Martin B.R., Mechoulam R., and Pertwee R.G. Pharmacol. Rev. 54 (2002) 161-202
4. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., and Mechoulam R. Science 258 (1992) 1946-1949
5. 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., et al. Biochem. Pharmacol. 50 (1995) 83-90
6. Pertwee R.G. Br. J. Pharmacol. 152 (2007) 984-986
7. Di Marzo V. Nat. Rev. Drug Discov. 7 (2008) 438-455
8. Fu J., Gaetani S., Oveisi F., Lo Verme J., Serrano A., Rodriguez De Fonseca F., Rosengarth A., Luecke H., Di Giacomo B., Tarzia G., and Piomelli D. Nature 425 (2003) 90-93
9. Cano C., Pavon J., Serrano A., Goya P., Paez J.A., de Fonseca F.R., and Macias-Gonzalez M. J. Med. Chem. 50 (2007) 389-393
10. Maccarrone M. Curr. Pharm. Des. 12 (2006) 759-772
11. Paquin A.M. Angew. Chem. 60 (1948) 316-320
12. Mc Dermott S.D.S., and Spillane W.J. Org. Prep. Proced. Int. (1984) 49-77
13. Atkins Jr. G.M., and Burgess E.M. J. Am. Chem. Soc. 94 (1972) 6135-6141
14. Lin S., Khanolkar A.D., Fan P., Goutopoulos A., Qin C., Papahadjis D., and Makriyannis A. J. Med. Chem. 41 (1998) 5353-5361
15. Kepler C.R., Tucker W.P., and Tove S.B. J. Biol. Chem. 245 (1970) 3612-3620
16. Winum J.Y., Toupet L., Barragan V., Dewynter G., and Montero J.L. Org. Lett. 3 (2001) 2241-2243
17. Kloek J.A., and Leschinsky K.L. J. Org. Chem. 41 (1976) 4028-4029
18. Hirst R.A., Almond S.L., and Lambert D.G. Neurosci. Lett. 220 (1996) 101-104
19. Pertwee R.G., Griffin G., Lainton J.A., and Huffman J.W. Eur. J. Pharmacol. 284 (1995) 241-247
20. Segall Y., Quistad G.B., Nomura D.K., and Casida J.E. Bioorg. Med. Chem. Lett. 13 (2003) 3301-3303
21. Melck D., Bisogno T., De Petrocellis L., Chuang H., Julius D., Bifulco M., and Di Marzo V. Biochem. Biophys. Res. Commun. 262 (1999) 275-284
22. Appendino G., Cascio M.G., Bacchiega S., Moriello A.S., Minassi A., Thomas A., Ross R., Pertwee R., De Petrocellis L., and Di Marzo V. FEBS Lett. 580 (2006) 568-574
23. Hughes J., Smith T.W., Kosterlitz H.W., Fothergill L.A., Morgan B.A., and Morris H.R. Nature 258 (1975) 577-580
24. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099-3108
25. Bradford M.M. Anal. Biochem. 72 (1976) 248-254
26. Desarnaud F., Cadas H., and Piomelli D. J. Biol. Chem. 270 (1995) 6030-6035