5-bromo-2'-deoxyuridine 5'-(N-(2-((2-cyclohexylethyl)amino)ethyl)glycyl ester) dihydrochloride | 130328-09-5

• 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-bromo-2'-deoxyuridine 5'-(N-(2-((2-cyclohexylethyl)amino)ethyl)glycyl ester) dihydrochloride
• 英文别名: 5-bromo-2'-deoxyuridine 5'-ethyl>glycyl ester> dihydrochloride；5-bromo-2'-deoxyuridine 5'-(N-{2-[(2-cyclohexylethyl)amino]ethyl}glycyl ester) dihydrochloride
• CAS: 130328-09-5
• 化学式: C₂₁H₃₃BrN₄O₆*2ClH
• 分子量: 590.342
• InChiKey: YAMRSKDLEQUJJJ-QQBJDQAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  134.68
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2'-deoxyuridine 5'-(N-(2-((2-cyclohexylethyl)amino)ethyl)glycyl ester) dihydrochloride 在 sodium hydroxide 、 phosphate buffer 作用下， 反应 7.0h， 生成 1-(2-环己基乙基)-2-哌嗪酮 、 溴脲苷
  参考文献：
  名称：

  Cyclization-activated prodrugs. Basic esters of 5-bromo-2'-deoxyuridine

  摘要：

  Some 3'- and 5'-[[(alkylamino)ethyl]glycyl] esters of 5-bromo-2'-deoxyuridine were prepared and evaluated in vitro as progenitors of the parent alcohol. The esters proved to be relatively stable at low pH but released 5-bromo-2'-deoxyuridine cleanly at rates which were pH and structure dependent. These basic esters are examples of cyclization-activated prodrugs in which generation of active drug is not linked to enzymatic cleavage but rather results from an intramolecular cyclization-elimination reaction.

  DOI：

  10.1021/jm00171a038
• 作为产物：
  描述：

  5-bromo-3'-(4-methoxytrityl)-2'-deoxyuridine 5'-ethyl>glycyl ester> 在 盐酸 、 水 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 2.25h， 生成 5-bromo-2'-deoxyuridine 5'-(N-(2-((2-cyclohexylethyl)amino)ethyl)glycyl ester) dihydrochloride
  参考文献：
  名称：

  Cyclization-activated prodrugs. Basic esters of 5-bromo-2'-deoxyuridine

  摘要：

  Some 3'- and 5'-[[(alkylamino)ethyl]glycyl] esters of 5-bromo-2'-deoxyuridine were prepared and evaluated in vitro as progenitors of the parent alcohol. The esters proved to be relatively stable at low pH but released 5-bromo-2'-deoxyuridine cleanly at rates which were pH and structure dependent. These basic esters are examples of cyclization-activated prodrugs in which generation of active drug is not linked to enzymatic cleavage but rather results from an intramolecular cyclization-elimination reaction.

  DOI：

  10.1021/jm00171a038