[5-Fluoro-1-((2S,5R)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2,2,2-trichloro-ethyl ester | 203635-02-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [5-Fluoro-1-((2S,5R)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2,2,2-trichloro-ethyl ester
• CAS: 203635-02-3
• 化学式: C₁₂H₁₁Cl₃FN₃O₅
• 分子量: 402.594
• InChiKey: YZYWZFSREFEOKT-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102.68
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [5-Fluoro-1-((2S,5R)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2,2,2-trichloro-ethyl ester 在 四氮唑 、 间氯过氧苯甲酸 、 锌 作用下， 以 甲醇 为溶剂， 生成 Thioacetic acid S-(2-{(2-acetylsulfanyl-ethoxy)-[(2R,5S)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethoxy]-phosphoryloxy}-ethyl) ester
  参考文献：
  名称：

  Bis-S-acyl-2-thioethyl (sate)-bearing monophosphate prodrug of β-L-FD4C as potent anti-HBV agent

  摘要：

  The S-acyl-2-thioethyl (SATE)-bearing 5'-monophosphate prodrug of beta-L-FD4C (8) was synthesized and evaluated for its activity against HBV in the 2.2.15 cell line. This pronucleotide (8) exhibited an excellent inhibitory effect against HBV with an EC50 value that is more than eight fold lower than that of the parent nucleoside (4) under some assay conditions. It is also important to note that pronucleotide (8) was capable of inhibiting HBV replication by 90%; whereas its parent, beta-L-FD4C (4), could only inhibit virus replication no greater than 70% in the same assay. When evaluated in the standard cytotoxicity assay in CEM cell line, pronucleotide (8) exhibited an IC50 value of 52 mu M, which was four times less toxic than parent beta-L-FD4C (4) (IC50 = 13 mu M). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10178-0
• 作为产物：
  描述：

  {1-[(2S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid 2,2,2-trichloro-ethyl ester 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到[5-Fluoro-1-((2S,5R)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Bis-S-acyl-2-thioethyl (sate)-bearing monophosphate prodrug of β-L-FD4C as potent anti-HBV agent

  摘要：

  The S-acyl-2-thioethyl (SATE)-bearing 5'-monophosphate prodrug of beta-L-FD4C (8) was synthesized and evaluated for its activity against HBV in the 2.2.15 cell line. This pronucleotide (8) exhibited an excellent inhibitory effect against HBV with an EC50 value that is more than eight fold lower than that of the parent nucleoside (4) under some assay conditions. It is also important to note that pronucleotide (8) was capable of inhibiting HBV replication by 90%; whereas its parent, beta-L-FD4C (4), could only inhibit virus replication no greater than 70% in the same assay. When evaluated in the standard cytotoxicity assay in CEM cell line, pronucleotide (8) exhibited an IC50 value of 52 mu M, which was four times less toxic than parent beta-L-FD4C (4) (IC50 = 13 mu M). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10178-0