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【结 构 式】

【药物名称】

【化学名称】5-[4-[2-[1-(Biphenyl-4-yl)ethylideneaminooxy]ethoxy]benzyl]thiazolidine-2,4-dione

【CA登记号】

【 分 子 式 】C26H24N2O4S

【 分 子 量 】460.55618

【开发单位】Sankyo (Originator)

【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, PPARgamma Agonists

合成路线1

This compound has been obtained by two related ways: 1) The condensation of 4-acetylbiphenyl oxime (I) with 2-(2-bromoethoxy)tetrahydropyran (II) by means of K2CO3 in hot dimethylacetamide gives the oxime derivative (III), which is treated with TsOH in methanol yielding 4-acetylbiphenyl O-(2-hydroxyethyl)oxime (IV). The condensation of (IV) with 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (V) by means of diethyl azodicarboxylate (DEAD) and PPh3 in THF affords (VI), the trityl derivative of the target compound, which is finally treated with hot aqueous ethanol to eliminate the trityl group. 2) The condensation of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (VIII) with N-(2-hydroxyethoxy)phthalimide (VII) by means DEAD gives the adduct (IX), which is treated with hydrazine to eliminate the phthalimido group yielding the substituted hydroxylamine (X). Finally, this compound is condensed with 4-acetylbiphenyl (XI) by means of TEA.

1 Yanagisawa, H.; Fujita, T.; Fujimoto, K.; Yoshioka, T.; Wada, K.; Oguchi, M.; Fujiwara, T.; Horikoshi, H. (Sankyo Co., Ltd.); Oxime derivs., their preparation and their therapeutic use. CA 2159938; EP 0708098; JP 1997048779; US 5703096; US 5780490; US 5972959 .
2 Isobe, A.; Fujita, S.; Fujiwara, T.; Yanagisawa, H.; Takamura, M.; Yamada, E.; Hagisawa, Y.; Yachi, M.; Novel oximes having 5-benzyl-2,4-thiazolidinedione as antihyperglycemic agents: Synthesis and structure-activity relationship. Bioorg Med Chem Lett 2000, 10, 4, 373.
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) 36912 1-[1,1'-biphenyl]-4-yl-1-ethanone oxime C14H13NO 详情 详情
(II) 26934 2-bromoethyl tetrahydro-2H-pyran-2-yl ether C7H13BrO2 详情 详情
(III) 36913 1-[1,1'-biphenyl]-4-yl-1-ethanone O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]oxime C21H25NO3 详情 详情
(IV) 36914 1-[1,1'-biphenyl]-4-yl-1-ethanone O-(2-hydroxyethyl)oxime C16H17NO2 详情 详情
(V) 18803 5-(4-hydroxybenzyl)-3-trityl-1,3-thiazolidine-2,4-dione C29H23NO3S 详情 详情
(VI) 36915 5-[4-[2-([[(E)-1-[1,1'-biphenyl]-4-ylethylidene]amino]oxy)ethoxy]benzyl]-3-trityl-1,3-thiazolidine-2,4-dione C45H38N2O4S 详情 详情
(VII) 36908 2-(2-hydroxyethoxy)-1H-isoindole-1,3(2H)-dione C10H9NO4 详情 详情
(VIII) 26462 5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione 74772-78-4 C10H9NO3S 详情 详情
(IX) 36909 2-(2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethoxy)-1H-isoindole-1,3(2H)-dione C20H16N2O6S 详情 详情
(X) 36910 5-[4-[2-(aminooxy)ethoxy]benzyl]-1,3-thiazolidine-2,4-dione C12H14N2O4S 详情 详情
(XI) 36916 1-[1,1'-biphenyl]-4-yl-1-ethanone 92-91-1 C14H12O 详情 详情
Extended Information