2-(pivaloylamino)-4(3H)-oxo-6-iodo-7-tosyl-7H-pyrrolo<2,3-d>pyrimidine | 173850-07-2

• 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: 2-(pivaloylamino)-4(3H)-oxo-6-iodo-7-tosyl-7H-pyrrolo<2,3-d>pyrimidine
• 英文别名: N-[6-iodo-7-(4-methylphenyl)sulfonyl-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethylpropanamide
• CAS: 173850-07-2
• 化学式: C₁₈H₁₉IN₄O₄S
• 分子量: 514.344
• InChiKey: XKZJGTCFFFKDTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(pivaloylamino)-4(3H)-oxo-6-iodo-7-tosyl-7H-pyrrolo<2,3-d>pyrimidine 在 platinum(IV) oxide copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,7-dihydro-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
• 作为产物：
  描述：

  对甲苯磺酰氯 、 6-iodo-4(3H)-oxo-2-pivaloylamino-7H-pyrrolo<2,3-d>pyrimidine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到2-(pivaloylamino)-4(3H)-oxo-6-iodo-7-tosyl-7H-pyrrolo<2,3-d>pyrimidine
  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