3',5'-di-O-p-toluoyl-5-(N-tert-butyloxycarbonylindol-2-yl)-2'-deoxyuridine | 873204-55-8

• 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: 3',5'-di-O-p-toluoyl-5-(N-tert-butyloxycarbonylindol-2-yl)-2'-deoxyuridine
• CAS: 873204-55-8
• 化学式: C₃₈H₃₇N₃O₉
• 分子量: 679.726
• InChiKey: VBUYJMANKWVFEL-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  50.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  147.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-p-toluoyl-5-(N-tert-butyloxycarbonylindol-2-yl)-2'-deoxyuridine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 5-(N-tert-butyloxycarbonylindol-2-yl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives

  摘要：

  We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 = 3 mu M. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used as nucleoside reference compound. Considering the cytotoxicity of synthetic compounds on peritoneal murine macrophages., the most toxic compound was MeThio-dU (3d) with a MTC at 10 mu M. Only Methia-dU (3b) was active against intramacrophagic amastigotes with an IC50 = 6.5 mu M. This latter can now be evaluated in vivo, for further investigations through structure-based drug design. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.07.001
• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 、 tributylstannane 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以43%的产率得到3',5'-di-O-p-toluoyl-5-(N-tert-butyloxycarbonylindol-2-yl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives

  摘要：

  We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 = 3 mu M. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used as nucleoside reference compound. Considering the cytotoxicity of synthetic compounds on peritoneal murine macrophages., the most toxic compound was MeThio-dU (3d) with a MTC at 10 mu M. Only Methia-dU (3b) was active against intramacrophagic amastigotes with an IC50 = 6.5 mu M. This latter can now be evaluated in vivo, for further investigations through structure-based drug design. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.07.001