5-bromo-5'-<(isobutyloxy)carbonyl>-2'-deoxyuridine | 130328-04-0

• 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-5'-<(isobutyloxy)carbonyl>-2'-deoxyuridine
• 英文别名: [(2R,3S,5R)-5-(5-bromo-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 2-methylpropyl carbonate
• CAS: 130328-04-0
• 化学式: C₁₄H₁₉BrN₂O₇
• 分子量: 407.218
• InChiKey: GNLLPTCGLUJCHG-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119.85
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-bromo-5'-<(isobutyloxy)carbonyl>-2'-deoxyuridine 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 5-bromo-3'-(4-methoxytrityl)-2'-deoxyuridine 5'-ethyl>glycyl ester>
  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：

  溴脲苷 、 氯甲酸异丁酯 在 吡啶 作用下， 反应 18.0h， 以62%的产率得到5-bromo-5'-<(isobutyloxy)carbonyl>-2'-deoxyuridine
  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

文献信息

• SAARI, WALFRED S.;SCHWERING, JOHN E.;LYLE, PAULETTE A.;SMITH, STEVEN J.;E+, J. MED. CHEM., 33,(1990) N, C. 2590-2595
  作者：SAARI, WALFRED S.、SCHWERING, JOHN E.、LYLE, PAULETTE A.、SMITH, STEVEN J.、E+

  DOI：——

  日期：——
• Cyclization-activated prodrugs. Basic esters of 5-bromo-2'-deoxyuridine
  作者：Walfred S. Saari、John E. Schwering、Paulette A. Lyle、Steven J. Smith、Edward L. Engelhardt

  DOI：10.1021/jm00171a038

  日期：1990.9

  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.