benzyl (2S)-2-[[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[(2S)-1-oxo-1-phenylmethoxypropan-2-yl]amino]phosphoryl]amino]propanoate | 1609239-20-4

• 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: benzyl (2S)-2-[[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[(2S)-1-oxo-1-phenylmethoxypropan-2-yl]amino]phosphoryl]amino]propanoate
• CAS: 1609239-20-4
• 化学式: C₃₀H₃₆FN₄O₉P
• 分子量: 646.609
• InChiKey: OVXBGBJWDYKKPN-XEJWYGKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3’-脱氧-3-氟胸苷 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 benzyl (2S)-2-[[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[(2S)-1-oxo-1-phenylmethoxypropan-2-yl]amino]phosphoryl]amino]propanoate
  参考文献：
  名称：

  Synthesis, anti-HIV and cytostatic evaluation of 3′-deoxy-3′-fluorothymidine (FLT) pro-nucleotides

  摘要：

  A series of pro-nucleotide phosphoramidates and phosphorodiamidates of the antiviral lead compound 3 '-deoxy-3 '-fluorothymidine (FLT) have been designed and synthesized. In vitro antiretroviral and cytostatic studies revealed potent (sub-micromolar) inhibition of HIV-1 and HIV-2 replication, with retention of activity in thymidine kinase-negative cell models, as predicted by the ProTide concept. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.092

文献信息

• Synthesis, anti-HIV and cytostatic evaluation of 3′-deoxy-3′-fluorothymidine (FLT) pro-nucleotides
  作者：Winnie Velanguparackel、Nadège Hamon、Jan Balzarini、Christopher McGuigan、Andrew D. Westwell

  DOI：10.1016/j.bmcl.2014.03.092

  日期：2014.5

  A series of pro-nucleotide phosphoramidates and phosphorodiamidates of the antiviral lead compound 3 '-deoxy-3 '-fluorothymidine (FLT) have been designed and synthesized. In vitro antiretroviral and cytostatic studies revealed potent (sub-micromolar) inhibition of HIV-1 and HIV-2 replication, with retention of activity in thymidine kinase-negative cell models, as predicted by the ProTide concept. (C) 2014 Elsevier Ltd. All rights reserved.