Ganstigmine hydrochloride, CHF-2819
Chemical Name: N-(2-Ethylphenyl)carbamic acid (4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-yl ester hydrochloride; N-(2-Ethylphenyl)geneserine hydrochloride
CAS No. 223585-99-7
项目整合开发状态: Phase II
项目研究机构: Chiesi (Originator)
合成路线:The oxidation of eserine (I) by means of H2O2 and KHCO3 produced the geneseroline carbamate (II),which was hydrolyzed to geneseroline (III) employing 62% sulfuric acid at 85 C.The desired carbamate was then obtained by condensation of (III) with 2-ethylphenyl isocyanate (IV) either in the presence of K2CO3 in acetone or in the presence of t-BuOK under sonication,and the title compound was then isolated as the corresponding hydrochloride salt.
合成路线:An alternative procedure for the preparation of the intermediate geneseroline (III) consisted in the oxidation of eseretole (V) to geneseretole (VI),followed by ether cleavage by means of concentrated sulfuric acid.
📌 参考资料/链接：
参考文献标题:A process for the preparation of aminocarbonyl derivs.of geneseroline having selective brain anticholinesterase activity
文献作者:Ventura,P.; Pighi,R.; Servadio,V.; Pietra,C.; Amari,G.; Salsi,B.; Pivetti,F.; Delcanale,M.; Chiesi,P.; Villetti,G.(Chiesi Farmaceutici SpA)
参考来源:WO 9919329
📄 详细内容
合成路线:The reaction of 2'-ethylphenserine (I) with MCPBA in chloroform gives the intermediate (II),which is treated in basic medium to yield the target geneserine derivative.
参考文献标题:Anticholinesterase activity of compounds related to geneserine tautomers.N-Oxides and 1,2-oxazines
文献作者:Yu,Q.-S.; Zhu,X.; Holloway,H.W.; Whittaker,N.F.; Brossi,A.; Greig,N.H.
参考来源:J Med Chem 2002,45(17),3684
产品链接: CAS No. 223585-99-7››