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【结 构 式】 
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【药物名称】Fiacitabine, FIAC 【化学名称】1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine 【CA登记号】69123-90-6, 69124-05-6 (monoHCl) 【 分 子 式 】C9H11FIN3O4 【 分 子 量 】371.10852 |
【开发单位】Sloan-Kettering Institute (Originator), Oclassen (Licensee) 【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
The reaction of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (I) with tris(trimethylsilyl)cytosine (II) in methylene chloride gives 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (III), which is hydrolyzed by treatment with methanol NH3 to afford 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (IV). Finally, this compound is iodinated by treatment with HIO3 - I2 in CCl4 - H2O - acetic acid.
| 【1】 Lopez, C.; Reichman, U.; Fox, J.; Hirota, K.; Watanabe, K.A.; Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. J Med Chem 1979, 22, 1, 21-24. |
| 【2】 Thorpe, P.J.; Castaner, J.; FIAC. Drugs Fut 1981, 6, 7, 410. |
| 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) | 29116 | [(2R,3R,4S,5S)-3-(acetoxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate | C14H14BrFO5 | 详情 | 详情 | |
| (II) | 37571 | 4-[bis(trimethylsilyl)amino]-1-(trimethylsilyl)-2(1H)-pyrimidinone | C13H29N3OSi3 | 详情 | 详情 | |
| (III) | 37572 | [(2R,3R,4S,5R)-3-(acetoxy)-5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-4-fluorotetrahydro-2-furanyl]methyl benzoate | C18H18FN3O6 | 详情 | 详情 | |
| (IV) | 37573 | 4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone | C9H12FN3O4 | 详情 | 详情 |