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【结 构 式】

【分子编号】13876

【品名】5-(2-Naphthylsulfanyl)-1,3-thiazolidine-2,4-dione

【CA登记号】

【 分 子 式 】C13H9NO2S2

【 分 子 量 】275.352

【元素组成】C 56.71% H 3.29% N 5.09% O 11.62% S 23.29%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

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