[Endocannabinoid 2-arachidonoylglycerol: 1,3-dinitrates of cyclooxygenase metabolites, synthesis and properties].
Glycerol esters 1,3-dinitrates of the cyclooxygenase metabolites of natural prostaglandin 2-arachidonoylglycerol, an endogenous ligand of cannabinoid receptors, were synthesized for the first time. Four methods of synthesis of these esters were developed via the activation of a carboxyl group and their chemical and pharmacological properties were investigated. The esters exhibit a more selective pharmacological spectrum of activities in comparison with the corresponding natural prostaglandins: some types of myotropic activity were enhanced, while others were loosened. 1,3-dinitroglycerol esters act as vasodilators, whereas the majority of natural prostaglandins act as vasoconstrictors. The observed changes result from the introduction of an NO-releasing fragment into prostaglandin molecule.
Serkov
I V
IV
Bezuglov
V V
VV
D001095:Arachidonic Acids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D004952:Esters; D005990:Glycerol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D009566:Nitrates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D011451:Prostaglandin-Endoperoxide Synthases / Q000737:chemistry* / Q000378:metabolism
D001095:Arachidonic Acids; D004952:Esters; D009566:Nitrates; D011451:Prostaglandin-Endoperoxide Synthases; D005990:Glycerol