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【结 构 式】

【药物名称】Semaxanib, Semoxind, TSU-16, NSC-696819, SU-5416

【化学名称】(Z)-3-(3,5-Dimethylpyrrol-2-ylmethylene)indolin-2-one

【CA登记号】204005-46-9

【 分 子 式 】C15H14N2O

【 分 子 量 】238.29163

【开发单位】Sugen (Originator), Esteve (Licensee), Taiho (Licensee), M.D. Anderson Cancer Center (Codevelopment)

【药理作用】Astrocytoma Therapy, Brain Cancer Therapy, Breast Cancer Therapy, Colorectal Cancer Therapy, Head and Neck Cancer Therapy, Kaposi's Sarcoma Therapy, Leukemia Therapy, Lung Cancer Therapy, Melanoma Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, Prostate Cancer Therapy, Angiogenesis Inhibitors, Flt3 (FLK2/STK1) Inhibitors, Inhibitors of Signal Transduction Pathways, VEGFR-2 (FLK-1/KDR) Inhibitors

合成路线1

Vilsmeier reaction between 2,4-dimethylpyrrole (I) and dimethylformamide (II) by means of phosphorous oxychloride in dichloroethane provides carbaldehyde (III), which is then condensed with 2-indolinone (IV) in ethanol in the presence of piperidine.

1 Tang, P.C.; Sun, L.; McMahon, G.; Hirth, K.P.; Shawver, L.K. (Sugen, Inc.); Indolinone combinatorial libraries and related products and methods for the treatment of disease. EP 0929520; JP 2001503736; WO 9807695 .
2 Tang, P.C.; Sun, L.; McMahon, G. (Sugen, Inc.); Indolinone cpds. for the treatment of disease. EP 0769947; JP 2000026412; US 5780496; US 5792783; US 5880141; US 5883113; US 5883116; WO 9640116 .
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) 51236 2,4-Dimethylpyrrole 625-82-1 C6H9N 详情 详情
(II) 33491 Dimethylformamide 68-12-2 C3H7NO 详情 详情
(III) 51237 3,5-dimethyl-1H-pyrrole-2-carbaldehyde C7H9NO 详情 详情
(IV) 18699 1,3-dihydro-2H-indol-2-one 59-48-3 C8H7NO 详情 详情
Extended Information