新产品编号:1664773
Chemical Name: 3,5,11,11a-Tetrahydrothiazolo[2,3-c]-1,4-benzothiazepine-5,11(2H)-dione
项目整合开发状态: Biological Testing
项目研究机构: Achillion (Originator), National Institutes of Health (Originator), US Department of Health & Human Services (Originator)
合成路线:Treatment of 2,2'-dithiobis(benzoic acid) (I) with thionyl chloride produced the corresponding acid chloride (II),which was further condensed with thiazolidine-2-carboxylic acid (III) in the presence of Na2CO3 to furnish diamide (IV).Reductive cleavage of the disulfide group of (IV) by means of NaBH4 in refluxing EtOH yielded thiol (V).Finally,intramolecular cyclization of (V) to give the title tricyclic compound was achieved by treatment with carbonyl diimidazole in boiling THF.
📌 参考资料/链接：
参考文献标题:Thiazepine inhibitors of HIV-1 integrase
文献作者:Garofalo,A.; Pommier,Y.; Neamati,N.; Nacci,V.(US Department of Health & Human Services)
参考来源:WO 0068235
📄 详细内容
合成路线:Treatment of 2,2'-dithiobis(benzoic acid) (I) with thionyl chloride produced the corresponding acid chloride (II),which was further condensed with thiazolidine-2-carboxylic acid (III) in the presence of Na2CO3 to furnish diamide (IV).Reductive cleavage of the disulfide group of (IV) by means of NaBH4 in refluxing EtOH yielded thiol (V).Finally,intramolecular cyclization of (V) to give the title tricyclic compound was achieved by treatment with carbonyl diimidazole in boiling THF.
参考文献标题:Thiazolothiazepine inhibitors of HIV-1 integrase
文献作者:Neamati,N.; Turpin,J.A.; Winslow,H.E.; Christensen,J.L.; Williamson,K.; Orr,A.; Rice,W.G.; Pommier,Y.; Garofalo,A.; Brizzi,A.; Campiani,G.; Fiorini,I.; Nacci,V.
参考来源:J Med Chem 1999,42(17),3334