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【结 构 式】

【药物名称】TSU-68, SU-6668

【化学名称】(Z)-3-[2,4-Dimethyl-5-(2-oxo-2,3-dihydro-1H-indol-3-ylidenemethyl)-1H-pyrrol-3-yl]propionic acid

【CA登记号】252916-29-3

【 分 子 式 】C18H18N2O3

【 分 子 量 】310.35576

【开发单位】Sugen (Originator), Taiho (Licensee), Cancer Research UK (Codevelopment)

【药理作用】Oncolytic Drugs, Solid Tumors Therapy, Angiogenesis Inhibitors, FGFR Inhibitors, Inhibitors of Signal Transduction Pathways, PDGFR Inhibitors, VEGFR-2 (FLK-1/KDR) Inhibitors

合成路线1

Basic hydrolysis of the known 2,4-dimethyl-5-ethoxycarbonyl-3-(2-ethoxycarbonyl ethyl)pyrrole (I) and subsequent decarboxylation of the resulting diacid (II) in the presence of HCl furnished 2,4-dimethyl-3-pyrrolepropionic acid (III). Vilsmeier formylation of (III) employing dimethylformamide and POCl3 produced aldehyde (IV). The title compound was then obtained by condensation of aldehyde (IV) with oxindole (V) in the presence of pyrrolidine, followed by acid treatment of the intermediate (VI). Alternatively, direct condensation of aldehyde (IV) with oxindole (V) in the presence of NaOH gave rise to the title compound.

1 Tang, P.C.; Sun, L.; McMahon, G. (Sugen, Inc.); Pyrrole substd. 2-indolinone protein kinase inhibitors. WO 9961422 .
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) 39751 ethyl 4-(3-ethoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate C14H21NO4 详情 详情
(II) 39752 4-(2-carboxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid C10H13NO4 详情 详情
(III) 39753 3-(2,4-dimethyl-1H-pyrrol-3-yl)propionic acid C9H13NO2 详情 详情
(IV) 39754 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propionic acid C10H13NO3 详情 详情
(V) 18699 1,3-dihydro-2H-indol-2-one 59-48-3 C8H7NO 详情 详情
(VI) 39755 3-[2,4-dimethyl-5-[(2-oxo-2,3-dihydro-1H-indol-3-yl)(1-pyrrolidinyl)methyl]-1H-pyrrol-3-yl]propionic acid C22H27N3O3 详情 详情
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