Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate | 144750-85-6

• 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: Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate
• 英文别名: Dimethyl N-{4-[2-(2-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate
• CAS: 144750-85-6
• 化学式: C₂₁H₂₀N₆O₆
• 分子量: 452.426
• InChiKey: RFQGUASAWDYKQJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  182.41
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate 在 palladium on activated charcoal 氢气 作用下， 以 三氟乙酸 为溶剂， 反应 96.0h， 以56%的产率得到Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate
  参考文献：
  名称：

  Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)

  摘要：

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-{4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.

  DOI：

  10.1016/s0040-4020(01)80479-8
• 作为产物：
  描述：

  4-氯-1H-吡唑并[3,4-D]嘧啶-6-胺 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 溴 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate
  参考文献：
  名称：

  Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)

  摘要：

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-{4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.

  DOI：

  10.1016/s0040-4020(01)80479-8