4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-1-methyluracil | 110419-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-1-methyluracil
• 英文别名: [(1S,10R,11R,12R)-12-fluoro-4-methyl-5-oxo-8,13-dioxa-4,6-diazatricyclo[8.2.1.02,7]trideca-2,6-dien-11-yl] acetate
• CAS: 110419-24-4
• 化学式: C₁₂H₁₃FN₂O₅
• 分子量: 284.244
• InChiKey: UYTBEWRODKGJIJ-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  79.65
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-1-methyluracil 在 Dowex 50 (H⁺) 作用下， 以 水 为溶剂， 反应 3.0h， 以55%的产率得到1-methyl-5-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Nucleosides. 146. 1-Methyl-5-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil, the C-nucleoside isostere of the potent antiviral agent, 1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)thymine (FMAU). Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides. 6

  摘要：

  The synthesis of 5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil (1, C-FMAU), an isostere of the potent antiviral and antitumor nucleoside 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)thymine (2'-fluoro-5-methyl-ara-U or FMAU), was achieved. Pseudouridine (2) was converted into 4,5'-anhydro-3'-O-acetyl-2'-O-triflylpseudouridine (4), which was treated with tris(dimethylamino)sulfur (1+) difluorotrimethylsilicate (TASF) to give 4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1- methyluracil (5b) in 40% yield. Acid hydrolysis of the 4,5'-anhydro linkage of 5b with Dowex 50 (H+) afforded C-FMAU. The inhibitory activity of C-FMAU against HSV-1 and HSV-2 was about 10-fold less than that of FMAU in tissue culture. This compound, however, did not show significant activity in mice inoculated with HSV-1 or HSV-2.

  DOI：

  10.1021/jm00395a023
• 作为产物：
  描述：

  [(1S,10R,11R,12S)-11-acetyloxy-4-methyl-5-oxo-8,13-dioxa-4,6-diazatricyclo[8.2.1.02,7]trideca-2,6-dien-12-yl] 2,2,2-trifluoroacetate 生成 4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-1-methyluracil
  参考文献：
  名称：

  PANKIEWICZ, KRZYSZTOF W.;NAWROT, BARBARA;SOCHACKA, ELZBIETA;WATANABE, KYO+, 7TH SYMP. CHEM. NUCL. ACID COMPON., BECHYNE CASTLE, AUG. 30TH - SEPT. 5TH+

  摘要：

  DOI：

文献信息

• PANKIEWICZ, KRZYSZTOF W.;NAWROT, BARBARA;GADLER, HAKAN;PRICE, RICHARD W.;+, J. MED. CHEM., 30,(1987) N 12, 2314-2316
  作者：PANKIEWICZ, KRZYSZTOF W.、NAWROT, BARBARA、GADLER, HAKAN、PRICE, RICHARD W.、+

  DOI：——

  日期：——