1-(3-C-fluoromethyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl)-N4-benzoylcytosine | 1239479-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-C-fluoromethyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl)-N4-benzoylcytosine
• CAS: 1239479-12-9
• 化学式: C₃₃H₃₂FN₃O₇
• 分子量: 601.631
• InChiKey: QKHHYCFSKHUXAO-WKIOUMQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  117.98
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(3-C-fluoromethyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl)-N4-benzoylcytosine 在 甲醇 、 氨 作用下， 反应 24.0h， 以83%的产率得到1-(3-C-fluoromethyl-3,5-di-O-benzyl-β-D-ribofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides

  摘要：

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.002
• 作为产物：
  描述：

  N4-苯甲酰基胞嘧啶 、 3-C-fluoromethyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribofuranose 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以83%的产率得到1-(3-C-fluoromethyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl)-N4-benzoylcytosine
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides

  摘要：

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.002