{[10-(10-{[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester | 933448-55-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: {[10-(10-{[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester
• CAS: 933448-55-6
• 化学式: C₃₉H₆₇N₅O₁₀
• 分子量: 765.988
• InChiKey: YWSNJJOZDVWHFN-GTXBZULCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  54.0
• 可旋转键数：
  30.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  198.36
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  {[10-(10-{[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以42%的产率得到{[10-(10-{[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid
  参考文献：
  名称：

  Synthesis of tricarbonyl rhenium and technetium complexes of a 5′-carboxamide 5-ethyl-2′-deoxyuridine for selective inhibition of herpes simplex virus thymidine kinase 1

  摘要：

  Herpes simplex virus thymidine kinase type 1 (HSV1-TK) is frequently used as reporter protein in gene therapy. Our aim is to produce single photon emitting reporter probe based on technetium-99m. The synthesis of organometallic technetium and rhenium complexes of a 5'-carboxamide 5-ethyl-2'-deoxyuridine derivative able to selectively inhibit HSV1-TK is presented. The 5-ethyl-2'-deoxyuridine functionalized with a suitable tridentate chelating system at position 5' was synthesized from commercial 2'-deoxyuridine in seven steps. The 5-ethyl-2'-deoxyuridine derivative was labeled with the fac-M(CO)(3)-core (M = Tc, Re). The resulting rhenium complex was found to be a selective competitive inhibitor of HSV1-TK (K-i = 4.56 mu M). Inhibition of the human cytosolic thymidine kinase (hTK1) previously reported with organometallic rhenium and technetium complexes of 5'-carboxamide thymidine derivative was not observed. The uptake of the technetium-99m complex in transfected cells expressing HSV1-TK has been evaluated to assess its possible use as reporter. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.10.011
• 作为产物：
  描述：

  5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 sodium azide 、 四溴化碳 、 氢气 、 sodium methylate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、300.01 kPa 条件下， 反应 12.25h， 生成 {[10-(10-{[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of tricarbonyl rhenium and technetium complexes of a 5′-carboxamide 5-ethyl-2′-deoxyuridine for selective inhibition of herpes simplex virus thymidine kinase 1

  摘要：

  Herpes simplex virus thymidine kinase type 1 (HSV1-TK) is frequently used as reporter protein in gene therapy. Our aim is to produce single photon emitting reporter probe based on technetium-99m. The synthesis of organometallic technetium and rhenium complexes of a 5'-carboxamide 5-ethyl-2'-deoxyuridine derivative able to selectively inhibit HSV1-TK is presented. The 5-ethyl-2'-deoxyuridine functionalized with a suitable tridentate chelating system at position 5' was synthesized from commercial 2'-deoxyuridine in seven steps. The 5-ethyl-2'-deoxyuridine derivative was labeled with the fac-M(CO)(3)-core (M = Tc, Re). The resulting rhenium complex was found to be a selective competitive inhibitor of HSV1-TK (K-i = 4.56 mu M). Inhibition of the human cytosolic thymidine kinase (hTK1) previously reported with organometallic rhenium and technetium complexes of 5'-carboxamide thymidine derivative was not observed. The uptake of the technetium-99m complex in transfected cells expressing HSV1-TK has been evaluated to assess its possible use as reporter. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.10.011