N-(1,1-dimethylethoxycarbonyl)-N-<2-ethyl>glycine N-succinimide ester | 130327-94-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1,1-dimethylethoxycarbonyl)-N-<2-ethyl>glycine N-succinimide ester
• 英文别名: N-(1,1-Dimethylethoxycarbonyl)-N-[2-[N-(1,1-dimethylethoxycarbonyl)-N-ethylamino]-ethyl]glycine N-Hydroxysuccinimide Ester；(2,5-Dioxopyrrolidin-1-yl) 2-[2-[ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate
• CAS: 130327-94-5
• 化学式: C₂₀H₃₃N₃O₈
• 分子量: 443.497
• InChiKey: XNTFJTRJECHZES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(1,1-dimethylethoxycarbonyl)-N-<2-ethyl>glycine N-succinimide ester 在 4-二甲氨基吡啶 、 水 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 121.5h， 生成 5-bromo-2'-deoxyuridine 3'-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：

  N-羟基丁二酰亚胺 、 N-(1,1-dimethylethoxycarbonyl)-N-<2-ethyl>glycine 在 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以53%的产率得到N-(1,1-dimethylethoxycarbonyl)-N-<2-ethyl>glycine N-succinimide 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

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：——
• US4942226A
  申请人：——

  公开号：US4942226A

  公开（公告）日：1990-07-17
• 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.