(S)-2-{5-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylethynyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid diethyl ester | 188186-05-2

• 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: (S)-2-{5-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylethynyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid diethyl ester
• 英文别名: diethyl (2S)-2-[6-[2-[2-(2,2-dimethylpropanoylamino)-4-oxo-3H-pyrido[2,3-d]pyrimidin-6-yl]ethynyl]-3-oxo-1H-isoindol-2-yl]pentanedioate
• CAS: 188186-05-2
• 化学式: C₃₁H₃₃N₅O₇
• 分子量: 587.632
• InChiKey: SPWUHSGDGYTULU-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2-{5-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylethynyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid diethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 68.0h， 生成 (S)-2-(5-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid diethyl ester
  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：

  谷氨酸二乙酯 在 钯 2,3,5-三甲基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-{5-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylethynyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid diethyl ester
  参考文献：
  名称：

  Novel synthesis of a conformationally-constrained analog of DDATHF

  摘要：

  A conformationally-constrained analog of DDATHF, in which the glutamate moiety is tied back to the benzoyl ring through an isoindolinone ring has been synthesized through a series of steps which commence with a Diels-Alder reaction of the Danishefsky diene with 4,4-diethoxybut-2-ynal. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02397-0