|
【结 构 式】 
|
【药物名称】AY-31637 【化学名称】5-(2-Naphthylsulfonyl)-2,4-thiazolidinedione 【CA登记号】125518-46-9 【 分 子 式 】C13H9NO4S2 【 分 子 量 】307.34898 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS |
合成路线1
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.
| 【1】 Zask, A.; Jirkovsky, I. (American Home Products Corp.); 5-[(1- and 2-Naphthalenyl)sulfonyl]-2,4-thiazolidinediones and derivs. Thereof. US 4997948 . |
| 【2】 McCaleb, M.L.; Jirkovsky, I.; Zask, A.; Nowicki, J.W.; Synthesis and antihyperglycemic activity of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones. J Med Chem 1990, 33, 5, 1418-23. |
| 【3】 Zask, A.; McCaleb, M.L.; AY-31,637. Drugs Fut 1991, 16, 6, 505. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (II) | 13875 | 5-Bromo-1,3-thiazolidine-2,4-dione | C3H2BrNO2S | 详情 | 详情 | |
| (III) | 15234 | 2-Naphthalenethiol; 2-Naphthylhydrosulfide | 91-60-1 | C10H8S | 详情 | 详情 |
| (IV) | 13876 | 5-(2-Naphthylsulfanyl)-1,3-thiazolidine-2,4-dione | C13H9NO2S2 | 详情 | 详情 | |
| (V) | 13877 | 3,5-Dilithiothiazolidine-2,4-dione | C3HLi2NO2S | 详情 | 详情 | |
| (VI) | 27989 | 2-naphthalenesulfonyl chloride | 93-11-8 | C10H7ClO2S | 详情 | 详情 |
Extended Information