Synthesis and pharmacological evaluation of sulfamide-based analogues of anandamide.
Arachidonyl and linoleyl sulfamide derivatives have been synthesized and their potential cannabimimetic properties evaluated in in vitro functional and binding assays. Replacement of the ethanolamide moiety of anandamide by -CH(2)NHSO(2)NH-R considerably reduces the CB1 receptor activity and only some of the compounds showed modest cannabinoid properties in binding assays. The new compounds were also tested as inhibitors of the FAAH enzyme but were inactive.
Cano
Carolina
C
Instituto de Química Médica, CSIC, Juan de la Cierva 3, Madrid 28006, Spain.
Páez
Juan Antonio
JA
Goya
Pilar
P
Serrano
Antonia
A
Pavón
Javier
J
Rodríguez de Fonseca
Fernando
F
Suardíaz
Margarita
M
Martín
María Isabel
MI
D000581:Amidohydrolases / Q000037:antagonists & inhibitors; D000818:Animals; D001095:Arachidonic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D063385:Cannabinoid Receptor Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002478:Cells, Cultured; D063388:Endocannabinoids; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D053284:Polyunsaturated Alkamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013449:Sulfonamides; D014649:Vas Deferens / Q000187:drug effects; D000099252:Fatty Acid Amide Hydrolases
D000581:Amidohydrolases; D001095:Arachidonic Acids; D063385:Cannabinoid Receptor Modulators; D063388:Endocannabinoids; D004791:Enzyme Inhibitors; D053284:Polyunsaturated Alkamides; D013449:Sulfonamides; D000099252:Fatty Acid Amide Hydrolases; C078814:anandamide