4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethyl}-benzoic acid methyl ester | 173850-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethyl}-benzoic acid methyl ester
• 英文别名: methyl 4-[2-[2-(2,2-dimethylpropanoylamino)-7-(4-methylphenyl)sulfonyl-4-oxo-5,6-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]ethyl]benzoate
• CAS: 173850-10-7
• 化学式: C₂₈H₃₂N₄O₆S
• 分子量: 552.651
• InChiKey: XPEZAZPKYILYIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethyl}-benzoic acid methyl ester 在 硫酸 作用下， 反应 1.5h， 以93%的产率得到4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic 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：

  4-乙炔基苯甲酸甲酯 在 palladium dihydroxide copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 15.0h， 生成 4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethyl}-benzoic acid methyl ester
  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

文献信息

• Synthesis of <i>N</i>-{4-[2-(2-Amino-5,6-dihydro-4(3<i>H</i>)-oxo-7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidin-6-yl)- ethyl]benzoyl}-<scp>l</scp>-glutamic Acid:  A Ring-Contracted Analogue of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid
  作者：Edward C. Taylor、Wendy B. Young、Carsten Spanka

  DOI：10.1021/jo951471k

  日期：1996.1.1

  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).