合成路线:The alkylation of 2-(methylsulfanyl)benzothiazole (I) with methyl p-toluenesulfonate in anisole gives 3-methyl-2-(methylsulfanyl)benzothiazolium p-toluenesulfonate (II),which is condensed with 3-ethyl-2-thioxothiazolidin-4-one (III) by means of triethylamine in acetonitrile to yield 3-ethyl-5-(3-methyl-2,3-dihydrobenzothiazol-2-ylidene)-2-thioxothiazolidin-4-one (IV).The methylation of (IV) with methyl p-toluenesulfonate in DMF affords 3-ethyl-5-(3-methyl-2,3-dihydrobenzothiazol-2-ylidene)-2-(methylsulfanyl)-4-oxo-4,5-dihydrothiazolium p-toluenesulfonate (V) (1),which is condensed with 1-ethyl-2-methylpyridinium p-toluenesulfonate (VI) by means of triethylamine in warm acetonitrile giving the p-toluenesulfonate of MKT-077 (VII).Finally,this compound is passed through an ion-exchange resin (Amberlyst A-26) in methanol/chloroform.
参考文献标题:MKT-077
文献作者:Wrobleski,T.; Castar,J.; Graul,A.
参考来源:Drugs Fut 1998,23(1),24
合成路线:The alkylation of 2-(methylsulfanyl)benzothiazole (I) with methyl p-toluenesulfonate in anisole gives 3-methyl-2-(methylsulfanyl)benzothiazolium p-toluenesulfonate (II),which is condensed with 3-ethyl-2-thioxothiazolidin-4-one (III) by means of triethylamine in acetonitrile to yield 3-ethyl-5-(3-methyl-2,3-dihydrobenzothiazol-2-ylidene)-2-thioxothiazolidin-4-one (IV).The methylation of (IV) with methyl p-toluenesulfonate in DMF affords 3-ethyl-5-(3-methyl-2,3-dihydrobenzothiazol-2-ylidene)-2-(methylsulfanyl)-4-oxo-4,5-dihydrothiazolium p-toluenesulfonate (V) (1),which is condensed with 1-ethyl-2-methylpyridinium p-toluenesulfonate (VI) by means of triethylamine in warm acetonitrile giving the p-toluenesulfonate of MKT-077 (VII).Finally,this compound is passed through an ion-exchange resin (Amberlyst A-26) in methanol/chloroform.
合成路线:N-Methylation of 2-(methylsulfanyl)benzothiazole (I) using methyl p-toluenesulfonate afforded iminium salt (II),which was condensed with 3-ethyl-4-oxothiazolidine-2-thione (III) to give the benzothiazolinylidene dervative (IV).Subsequent S-methylation of (IV) to produce the 3-ethyl-2-(methylthio)thiazolinium salt (V) was followed by condensation with 2,4-dimethyl-3-ethylthiazolium salt (VI) in the presence of Et3N,yielding the triheterocyclic system (VIII) as the p-toluenesulfonate salt.Finally,conversion to the title chloride salt was achieved by means of an anionic exchange resin.
参考文献标题:Structure-activity of novel rhodacyanine dyes as antitumor agents
文献作者:Ikegawa,A.; Kawakami,M.; Ogawa,K.; Shishido,T.; Chen,L.B.; Tatsuta,N.; Ukai,T.; Koya,K.
参考来源:J Med Chem 1998,41(1),130
产品链接: CAS No. 147366-41-4››