• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】IDD-598

【化学名称】2-[5-Fluoro-2-[N-(3-nitrobenzyl)thiocarbamoyl]phenoxy]acetic acid

【CA登记号】

【 分 子 式 】C16H13FN2O5S

【 分 子 量 】364.35481

【开发单位】Institute for Diabetes Discovery (Originator)

【药理作用】ENDOCRINE DRUGS, Symptomatic Antidiabetic Agents, Treatment of Diabetic Complications, Aldose Reductase Inhibitors

合成路线1

Treatment of 2,4-difluorophenylacetic acid (I) with NaOH in dimethylimidazolinone at 135 C afforded 4-fluorosalicylic acid (II). After activation of (II) with SOCl2, coupling with 3-nitrobenzylamine (III) gave amide (IV). Subsequent O-alkylation of (IV) by means of ethyl bromoacetate (A) and K2CO3 yielded ether (V). Conversion of the amide function of (V) to the corresponding thioamide (VI) was accomplished using phosphorus pentasulfide (P4S10) in pyridine. Finally, the ester group of (VI) was hydrolyzed with NaOH to the title carboxylic acid.

1 Van Zandt, M.C.; Sibley, E.O.; Combs, K.J.; et al.; Design and synthesis of novel inhibitors of aldose reductase for the treatment of diabetic complications. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 137.
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) 35123 2,4-difluorobenzoic acid 1583-58-0 C7H4F2O2 详情 详情
(II) 35124 4-fluoro-2-hydroxybenzoic acid 345-29-9 C7H5FO3 详情 详情
(III) 35125 (3-nitrophenyl)methanamine; 3-nitrobenzylamine C7H8N2O2 详情 详情
(IV) 35126 4-fluoro-2-hydroxy-N-(3-nitrobenzyl)benzamide C14H11FN2O4 详情 详情
(V) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(VI) 35127 ethyl 2-(5-fluoro-2-[[(3-nitrobenzyl)amino]carbonyl]phenoxy)acetate C18H17FN2O6 详情 详情
(VII) 35128 ethyl 2-(5-fluoro-2-[[(3-nitrobenzyl)amino]carbothioyl]phenoxy)acetate C18H17FN2O5S 详情 详情
Extended Information