diethyl (2S)-2-[5-[2-[2-(2,2-dimethylpropanoylamino)-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl]ethyl]-3-oxo-1H-isoindol-2-yl]pentanedioate | 191804-12-3

• 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 (2S)-2-[5-[2-[2-(2,2-dimethylpropanoylamino)-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl]ethyl]-3-oxo-1H-isoindol-2-yl]pentanedioate
• CAS: 191804-12-3
• 化学式: C₃₀H₃₇N₅O₇
• 分子量: 579.653
• InChiKey: NCCCKHVATWZZAX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl (2S)-2-[5-[2-[2-(2,2-dimethylpropanoylamino)-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl]ethyl]-3-oxo-1H-isoindol-2-yl]pentanedioate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 72.0h， 生成 (2S)-2-[5-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]-3-oxo-1H-isoindol-2-yl]pentanedioic acid
  参考文献：
  名称：

  Synthesis of Conformationally-Constrained Glutamate Analogues of the Antitumor Agents DDATHF, LY254155, and LY231514

  摘要：

  Analogues of the active antitumor agents DDATHF (4), LY254155 (11), and LY231514 (14) have been prepared in which the rotational flexibility of the benzoylglutamate amide linkage is constrained by incorporation of a methylene bridge between the glutamate amide nitrogen and the ortho position of the aromatic ring. Evaluation of the resulting isoindolinones as in vitro inhibitors of the growth of CCRF-CEM cells revealed that, although some analogues retained activity, in no case was cytotoxicity enhanced, and in some cases it was substantially reduced.

  DOI：

  10.1021/jo9703459
• 作为产物：
  描述：

  5-碘-2-甲基苯甲酸甲酯 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氢气 、 potassium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 80.0 ℃ 、344.73 kPa 条件下， 反应 9.5h， 生成 diethyl (2S)-2-[5-[2-[2-(2,2-dimethylpropanoylamino)-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl]ethyl]-3-oxo-1H-isoindol-2-yl]pentanedioate
  参考文献：
  名称：

  Synthesis of Conformationally-Constrained Glutamate Analogues of the Antitumor Agents DDATHF, LY254155, and LY231514

  摘要：

  Analogues of the active antitumor agents DDATHF (4), LY254155 (11), and LY231514 (14) have been prepared in which the rotational flexibility of the benzoylglutamate amide linkage is constrained by incorporation of a methylene bridge between the glutamate amide nitrogen and the ortho position of the aromatic ring. Evaluation of the resulting isoindolinones as in vitro inhibitors of the growth of CCRF-CEM cells revealed that, although some analogues retained activity, in no case was cytotoxicity enhanced, and in some cases it was substantially reduced.

  DOI：

  10.1021/jo9703459