AY-31637

5-萘-2-基磺酰基-1,3-噻唑烷-2,4-二酮Chemical Name: 5-(2-Naphthylsulfonyl)-2,4-thiazolidinedione
CAS No. 125518-46-9
项目整合开发状态: Preclinical
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:AY-31,637 may be synthesized by either of two routes:1) Dilithiation of 2,4-thiazolidinedione (I) with two equivalents of n-butyllithium,followed by sulfonylation with 2-naphthylsulfonyl chloride (VI).2) Coupling of 2-mercaptonaphthalene (III) and 5-bromo-2,4-thiazolidinedione (II) by the addition of two equivalents of lithium diisopropylamide gives 5-(2-naphthylthio)-2,4-thiazolidinedione (IV).Oxidation of this compound with excess hydrogen peroxide in acetic acid at 60 C gives the corresponding sulfone,AY-31,637.
📌 参考资料/链接:
参考文献标题:5-[(1- and 2-Naphthalenyl)sulfonyl]-2,4-thiazolidinediones and derivs.Thereof
文献作者:Zask,A.; Jirkovsky,I.(American Home Products Corp.)
参考来源:US 4997948

📄 详细内容


合成路线:AY-31,637 may be synthesized by either of two routes:1) Dilithiation of 2,4-thiazolidinedione (I) with two equivalents of n-butyllithium,followed by sulfonylation with 2-naphthylsulfonyl chloride (VI).2) Coupling of 2-mercaptonaphthalene (III) and 5-bromo-2,4-thiazolidinedione (II) by the addition of two equivalents of lithium diisopropylamide gives 5-(2-naphthylthio)-2,4-thiazolidinedione (IV).Oxidation of this compound with excess hydrogen peroxide in acetic acid at 60 C gives the corresponding sulfone,AY-31,637.

参考文献标题:Synthesis and antihyperglycemic activity of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones
文献作者:McCaleb,M.L.; Jirkovsky,I.; Zask,A.; Nowicki,J.W.
参考来源:J Med Chem 1990,33(5),1418-23


合成路线:AY-31,637 may be synthesized by either of two routes:1) Dilithiation of 2,4-thiazolidinedione (I) with two equivalents of n-butyllithium,followed by sulfonylation with 2-naphthylsulfonyl chloride (VI).2) Coupling of 2-mercaptonaphthalene (III) and 5-bromo-2,4-thiazolidinedione (II) by the addition of two equivalents of lithium diisopropylamide gives 5-(2-naphthylthio)-2,4-thiazolidinedione (IV).Oxidation of this compound with excess hydrogen peroxide in acetic acid at 60 C gives the corresponding sulfone,AY-31,637.
参考文献标题:AY-31,637
文献作者:Zask,A.; McCaleb,M.L.
参考来源:Drugs Fut 1991,16(6),505


产品链接: CAS No. 125518-46-9››