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【结 构 式】 
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【药物名称】CF-1368 【化学名称】3-(2'-Deoxy-beta-D-ribofuranosyl)-6-octyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one 【CA登记号】215668-64-7 【 分 子 式 】C19H28N2O5 【 分 子 量 】364.44541 |
【开发单位】Cardiff University (Originator), Rega Institute for Medical Research (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Anti-Varicella Zoster Virus Drugs, Antiviral Drugs |
合成路线1
Coupling of 5-iodo-2'-deoxyuridine (I) with 1-decyne (II) in the presence of cuprous iodide and tetrakis(triphenylphosphine)palladium furnished the 5-decynyl uridine derivative (III). This was then cyclized to the title furopyrimidinone by treatment with cuprous iodide and triethylamine in refluxing methanol.
| 【1】 Balzarini, J.; McGuigan, C.; Andrei, G.; Srinivasan, S.; Snoeck, R.; De clercq, E.; Bicyclic nucleoside inhibitors of varicella-Zoster virus (VZV): The effect of terminal unsaturation in the side chain. Bioorg Med Chem Lett 2001, 11, 3, 391. |
| 【2】 Brancale, A.; Snoeck, R.; Yarnold, C.J.; Barucki, H.; Velázquez, S.; Jones, G.; Andrei, G.; McGuigan, C.; De Clercq, E.; Balzarini, J.; Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. J Med Chem 1999, 42, 22, 4479. |
| 【3】 Jones, G.; Balzarini, J.; McGuigan, C.; Yarnold, C.; De Clercq, E. (University College, Cardiff); Anti-viral pyrimidine nucleoside analogues. EP 0980377; WO 9849177 . |
| 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) | 31154 | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione | 54-42-2 | C9H11IN2O5 | 详情 | 详情 |
| (II) | 42585 | 1-decyne | 764-93-2 | C10H18 | 详情 | 详情 |
| (III) | 42586 | 5-(1-decynyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C19H28N2O5 | 详情 | 详情 |
Extended Information