dimethyl (2S)-2-[[4-[2-[2-(2,2-dimethylpropanoylamino)-7-ethoxycarbonyl-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]ethynyl]benzoyl]amino]pentanedioate | 173850-16-3

• 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: dimethyl (2S)-2-[[4-[2-[2-(2,2-dimethylpropanoylamino)-7-ethoxycarbonyl-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]ethynyl]benzoyl]amino]pentanedioate
• CAS: 173850-16-3
• 化学式: C₃₀H₃₃N₅O₉
• 分子量: 607.62
• InChiKey: QRESKTWCAQAIHY-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dimethyl (2S)-2-[[4-[2-[2-(2,2-dimethylpropanoylamino)-7-ethoxycarbonyl-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]ethynyl]benzoyl]amino]pentanedioate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 53.0h， 生成 N-{4-[2-(2-amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)ethyl] benzoyl}-L-glutamic acid
  参考文献：
  名称：

  Synthesis of N-{4-[2-(2-Amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-6-yl)- ethyl]benzoyl}-l-glutamic Acid:  A Ring-Contracted Analogue of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid

  摘要：

  This paper describes the synthesis of N-(4-[2-(2-amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl) -L-glutamic acid (4), which can be viewed as a ring-contracted analogue of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF, 1) in which the C-7 methylene group of the latter has been excised and C-6 joined to N-8. This compound exhibits significant activity as an inhibitor of the growth of human (CCRF-CEM) lymphoblastic leukemic cells in vitro and apparently acts by blocking de novo purine biosynthesis through inhibition of glycinamide ribonucleotide formyltransferase (GAR FTase).

  DOI：

  10.1021/jo951471k
• 作为产物：
  描述：

  2-(pivaloylamino)-4(3H)-oxo-7-(ethoxycarbonyl)-7H-pyrrolo<2,3-d>pyrimidine 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.25h， 生成 dimethyl (2S)-2-[[4-[2-[2-(2,2-dimethylpropanoylamino)-7-ethoxycarbonyl-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]ethynyl]benzoyl]amino]pentanedioate
  参考文献：
  名称：

  Synthesis of N-{4-[2-(2-Amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-6-yl)- ethyl]benzoyl}-l-glutamic Acid:  A Ring-Contracted Analogue of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid

  摘要：

  This paper describes the synthesis of N-(4-[2-(2-amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl) -L-glutamic acid (4), which can be viewed as a ring-contracted analogue of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF, 1) in which the C-7 methylene group of the latter has been excised and C-6 joined to N-8. This compound exhibits significant activity as an inhibitor of the growth of human (CCRF-CEM) lymphoblastic leukemic cells in vitro and apparently acts by blocking de novo purine biosynthesis through inhibition of glycinamide ribonucleotide formyltransferase (GAR FTase).

  DOI：

  10.1021/jo951471k