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【结 构 式】 
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【药物名称】NSC-378901, IDX, I-DOX, FCE-21954, Iodo-Dox 【化学名称】4'-Deoxy-4'-iododoxorubicin 【CA登记号】83997-75-5 【 分 子 式 】C27H28INO10 【 分 子 量 】653.42931 |
【开发单位】Pfizer (Originator) 【药理作用】Antibiotics and Alkaloids, Antineoplastic Antibiotics, ONCOLYTIC DRUGS |
合成路线1
The reaction of 4'-epi-N-trifluoroacetyldaunorubicin (I) with trifluoro methanesulfonic anhydride gives the corresponding 4'-O-triflate (II), which is converted to 4'-deoxy-4'-iodo-N-trifluoroacetyldaunorubicin (III). The hydrolysis of (III) with NaOH affords 4'-deoxy-4'-iododaunorubicin (IV), which is finally brominated with Br2 and hydrolyzed with aqueous sodium formate.
| 【1】 Suarato, A.; Penco, S.; Casazza, A.M.; Arcamone, F. (Pharmacia Corp.); 4'-Iododerivatives of anthracycline glycosides. BE 0892943; DE 3214559; FR 2525225; GB 2118540; JP 58183698; US 4438105 . |
| 【2】 Suarato, A.; Penco, S.; Arcamone, F. (Pharmacia Corp.); Process for the preparation of 4'-deoxy-daunorubicin and 4'-deoxy-doxorubicin. EP 0048967; IT 1211116; US 4345070 . |
| 【3】 Castaner, R.M.; Serradell, M.N.; Nadhestani, A.N.; Castaner, J.; FCE-21954. Drugs Fut 1987, 12, 9, 849. |
| 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) | 28760 | N-Trifluoroacetyldaunomycin; N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide | C29H28F3NO11 | 详情 | 详情 | |
| (II) | 28761 | N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-iodo-2-[(trifluoromethyl)sulfonyl]tetrahydro-2H-pyran-4-yl]-2,2,2-trifluoroacetamide | C29H24F6INO12S | 详情 | 详情 | |
| (III) | 28762 | N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-iodo-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide | C29H27F3INO10 | 详情 | 详情 | |
| (IV) | 28763 | (8S,10S)-8-acetyl-10-[[(2R,4S,5S,6S)-4-amino-5-iodo-6-methyltetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | C27H28INO9 | 详情 | 详情 |
Extended Information