5-bromo-3'-(4-methoxytrityl)-2'-deoxyuridine | 130328-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-bromo-3'-(4-methoxytrityl)-2'-deoxyuridine
• 英文别名: 5-bromo-1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[(4-methoxyphenyl)-diphenylmethoxy]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 130328-06-2
• 化学式: C₂₉H₂₇BrN₂O₆
• 分子量: 579.447
• InChiKey: OQOOKBWNRZYEHE-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(1,1-dimethylethoxycarbonyl)-N-<2-ethyl>glycine 、 5-bromo-3'-(4-methoxytrityl)-2'-deoxyuridine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到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 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 22.5h， 生成 5-bromo-3'-(4-methoxytrityl)-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

• 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.