Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand.
Novel analogues of 2-arachidonoylglycerol (2-AG), an endogenous cannabinoid receptor ligand, were developed. Chemical synthesis of these analogues (2-AGA105 and 2-AGA109) was accomplished starting from 2-octyn-1-ol and diethyl malonate and employing Wittig coupling of triene phosphonate with an aldehyde intermediate in a convergent and stereoselective manner. These analogues should be useful lead compounds for the development of novel 2-AG mimetics.
Suhara
Y
Y
Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, 199-0195, Kanagawa, Japan.
Nakane
S
S
Arai
S
S
Takayama
H
H
Waku
K
K
Ishima
Y
Y
Sugiura
T
T
D000447:Aldehydes / Q000138:chemical synthesis; D001095:Arachidonic Acids; D002118:Calcium / Q000819:agonists*; D063388:Endocannabinoids; D005989:Glycerides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D018922:HL-60 Cells / Q000378:metabolism; D006801:Humans; D008024:Ligands; D008314:Malonates / Q000138:chemical synthesis*; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000819:agonists* / Q000378:metabolism; D013237:Stereoisomerism
D000447:Aldehydes; D001095:Arachidonic Acids; D063388:Endocannabinoids; D005989:Glycerides; D008024:Ligands; D008314:Malonates; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; C094503:glyceryl 2-arachidonate; C030978:diethylmalonic acid; D002118:Calcium