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【结 构 式】 
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【药物名称】ACEA, LS-63778 【化学名称】(all-Z)-N-(2-Chloroethyl)-5,8,11,14-icosatetraenamide 【CA登记号】 【 分 子 式 】C22H36ClNO 【 分 子 量 】365.99132 |
【开发单位】National Hellenic Research Foundation (Originator), University of Connecticut (Originator) 【药理作用】Cannabinoid CB1 Agonists |
合成路线1
Title compound was prepared by formation of the arachidonic acid chloride (II) upon treatment of the corresponding acid (I) with oxalyl chloride in CH2Cl2 containing DMF at 0 C, followed by condensation with 2-chloroethylamine - HCl (III) in the presence of pyridine.
| 【1】 Lin, S.; Khanolkar, A.D.; Fan, P.; Goutopoulos, A.; Qin, C.; Papahadjis, D.; Makriyannis, A.; Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J Med Chem 1998, 41, 27, 5353. |
合成路线2
Arachidonic acid (I) was converted to the mixed anhydride (II) upon treatment with isobutyl chloroformate and triethylamine. Subsequent condensation of (II) with 2-chloroethylamine (III) provided the target amide.
| 【1】 Murphy, V.; Greenberg, M.J.; Manna, S.; Dicamelli, R.; Ross, R.A.; Campbell, W.B.; Stevenson, L.A.; Hillard, C.J.; Pertwee, R.G.; Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J Pharmacol Exp Ther 1999, 289, 3, 1427. |
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