新产品编号:1087343
Chemical Name: [6-Methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl](3,4,5-trimethoxyphenyl)methanone
项目整合开发状态: Biological Testing
项目研究机构: Lilly (Originator), Baylor University (Codevelopment), National Cancer Institute (Codevelopment)
合成路线:Alkylation of 3-methoxybenzenethiol (I) with 4'-methoxyphenacyl bromide (II) afforded sulfide (III).Cyclization of (III) with concomitant rearrangement in the presence of polyphosphoric acid produced a mixture of regioisomers (IV) and (V) that were separated by their different solubility in acetone.Then,Friedel-Crafts acylation of the desired insoluble isomer (IV) with 3,4,5-trimethoxybenzoyl chloride (VI) in the presence of AlCl3 provided the title ketone,which was separated from some demethylated byproduct by means of silica gel chromatography.
📌 参考资料/链接：
参考文献标题:Novel benzothiophene cpds.and methods
文献作者:Carlson,D.G.; Cullinan,G.J.; Fahey,K.J.; Jackson,W.T.; Roehm,N.W.; Spaethe,S.M.(Eli Lilly and Company)
参考来源:EP 0732331; JP 1999501932; WO 9628156
📄 详细内容
合成路线:Alkylation of 3-methoxybenzenethiol (I) with 4'-methoxyphenacyl bromide (II) afforded sulfide (III).Cyclization of (III) with concomitant rearrangement in the presence of polyphosphoric acid produced a mixture of regioisomers (IV) and (V) that were separated by their different solubility in acetone.Then,Friedel-Crafts acylation of the desired insoluble isomer (IV) with 3,4,5-trimethoxybenzoyl chloride (VI) in the presence of AlCl3 provided the title ketone,which was separated from some demethylated byproduct by means of silica gel chromatography.
参考文献标题:Anti-mitotic agents which inhibit tubulin polymerization
文献作者:Pinney,K.G.(Baylor University)
参考来源:US 5886025
合成路线:Alkylation of 3-methoxybenzenethiol (I) with 4'-methoxyphenacyl bromide (II) afforded sulfide (III).Cyclization of (III) with concomitant rearrangement in the presence of polyphosphoric acid produced a mixture of regioisomers (IV) and (V) that were separated by their different solubility in acetone.Then,Friedel-Crafts acylation of the desired insoluble isomer (IV) with 3,4,5-trimethoxybenzoyl chloride (VI) in the presence of AlCl3 provided the title ketone,which was separated from some demethylated byproduct by means of silica gel chromatography.
参考文献标题:Hepatocyte gene therapy in a large animal: A neonatal bovine model of citrullinemia
文献作者:Lee,B.; Dennis,J.A.; Healy,P.J.; Mull,B.; Pastore,L.; Yu,H.; Aguilar-Cordova,E.; O'Brien,W.; Reeds,P.; Beaude,A.L.
参考来源:Proc Natl Acad Sci USA 1999,96(7),3981
合成路线:Alkylation of 3-methoxybenzenethiol (I) with 4'-methoxyphenacyl bromide (II) afforded sulfide (III).Cyclization of (III) with concomitant rearrangement in the presence of polyphosphoric acid produced a mixture of regioisomers (IV) and (V) that were separated by their different solubility in acetone.Then,Friedel-Crafts acylation of the desired insoluble isomer (IV) with 3,4,5-trimethoxybenzoyl chloride (VI) in the presence of AlCl3 provided the title ketone,which was separated from some demethylated byproduct by means of silica gel chromatography.
参考文献标题:Antiestrogens.2.Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone hydrochloride (LY156758),a remarkably effec
文献作者:Jones,C.D.; Jevnikar,M.G.; Pike,A.J.; Peters,M.K.; Black,L.J.; Thompson,A.R.; Falcone,J.F.; Clemens,J.A.
参考来源:J Med Chem 1984,27(8),1057