diethyl N-<2-pivaloylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate | 149765-22-0

• 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: diethyl N-<2-pivaloylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate
• CAS: 149765-22-0
• 化学式: C₂₉H₃₇N₅O₆
• 分子量: 551.643
• InChiKey: HGSBPDSOIDCXJP-QFIPXVFZSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152.37
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl N-<2-pivaloylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate 在 sodium hydroxide 作用下， 反应 72.0h， 以57%的产率得到N-<2-amino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamic acid
  参考文献：
  名称：

  The Synthesis of N-{2-Amino-4-substituted [(Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic Acids as Antineoplastic Agents

  摘要：

  A series of N-{2-amino-4-substituted[(pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acids were synthesized. In this current synthesis, compound 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (4) was selected as an important precursor for the preparation of key intermediates such as 5b, 10b, 15a and 15b. These highly functionalized pyrrolo[2,3-d]pyrimidines were then later coupled with either 4-ethynylbenzoylglutamate or 4-iodobenzoylglutamate in a palladium catalyzed Heck reaction and thus provided the basic skeleton of the targeted molecules. The availability of the chlorine atom at the 4-position of the pyrrolopyrimidine nucleus has allowed us to introduce different substituents at this position efficiently. By this approach, we were able to prepare a variety of 4-substituted pyrrolo[2,3d]pyrimidine based folate antagonists (2a-2g) which are closely related to the novel thymidylate synthase inhibitor LY231514. In vitro analysis has demonstrated that some of these agents are highly cytotoxic against human leukemic cells (CCRF-CEM) in culture.

  DOI：

  10.3987/com-92-s(t)65
• 作为产物：
  描述：

  diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以59%的产率得到diethyl N-<2-pivaloylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate
  参考文献：
  名称：

  The Synthesis of N-{2-Amino-4-substituted [(Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic Acids as Antineoplastic Agents

  摘要：

  A series of N-{2-amino-4-substituted[(pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acids were synthesized. In this current synthesis, compound 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (4) was selected as an important precursor for the preparation of key intermediates such as 5b, 10b, 15a and 15b. These highly functionalized pyrrolo[2,3-d]pyrimidines were then later coupled with either 4-ethynylbenzoylglutamate or 4-iodobenzoylglutamate in a palladium catalyzed Heck reaction and thus provided the basic skeleton of the targeted molecules. The availability of the chlorine atom at the 4-position of the pyrrolopyrimidine nucleus has allowed us to introduce different substituents at this position efficiently. By this approach, we were able to prepare a variety of 4-substituted pyrrolo[2,3d]pyrimidine based folate antagonists (2a-2g) which are closely related to the novel thymidylate synthase inhibitor LY231514. In vitro analysis has demonstrated that some of these agents are highly cytotoxic against human leukemic cells (CCRF-CEM) in culture.

  DOI：

  10.3987/com-92-s(t)65