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【结 构 式】 
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【药物名称】XL-119, DEAE-Rebeccamycin, NSC-D-640199(free base), NSC-655649, BMY-27557-14(tartrate), BMY-27557-01(HCl), BMS-181176 【化学名称】1,11-Dichloro-6-[2-(diethylamino)ethyl]-12-(4-O-methyl-beta-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione phosphate 【CA登记号】119673-08-4 (free base) 【 分 子 式 】C33H37Cl2N4O11P 【 分 子 量 】767.56284 |
【开发单位】Bristol-Myers Squibb (Originator), Exelixis (Licensee) 【药理作用】Antibiotics and Alkaloids, Antineoplastic Antibiotics, Brain Cancer Therapy, Breast Cancer Therapy, Colorectal Cancer Therapy, Liver Cancer Therapy, Lung Cancer Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, Renal Cancer Therapy, Solid Tumors Therapy |
合成路线1
Treatment of rebeccamycin (I) with 2-(diethylamino)ethyl chloride (II) and NaH in DMF at r.t. gave 8-N-(2-diethylaminoethyl)- rebeccamycin (III) (1). The target phosphate salt was then prepared by addition of H3PO4 to a suspension of (III) in water until a pH of 3-4.
| 【1】 Kaneko, T.; Wong, H.S.; Utzig, J.J. (Bristol-Myers Squibb Co.); Rebeccamycin analogs. AU 8781148; EP 0269025; JP 1988198695; US 4808613 . |
| 【2】 Venkataram, U.V. ; Franchini, M.K.; Bogardus, J.B. (Bristol-Myers Squibb Co.); Stable solutions of rebeccamycin analog and preparation thereof . EP 0397147 . |
| 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) | 19164 | 1,11-dichloro-12-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl]-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | C27H21Cl2N3O7 | 详情 | 详情 | |
| (II) | 16194 | 2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine | 100-35-6 | C6H14ClN | 详情 | 详情 |
| (III) | 19166 | 1,11-dichloro-6-[2-(diethylamino)ethyl]-12-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl]-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | C33H34Cl2N4O7 | 详情 | 详情 |