2-chloro-7-cyclopentyl-6-iodo-7H-pyrrolo[2,3-d]pyrimidine | 1383481-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-chloro-7-cyclopentyl-6-iodo-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 2-chloro-7-cyclopentyl-6-iodopyrrolo[2,3-d]pyrimidine
• CAS: 1383481-58-0
• 化学式: C₁₁H₁₁ClIN₃
• 分子量: 347.586
• InChiKey: FGOHOOPZXPLHTC-UHFFFAOYSA-N

物化性质

• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-7-cyclopentyl-6-iodo-7H-pyrrolo[2,3-d]pyrimidine 在 四(三苯基膦)钯 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [4-[[7-Cyclopentyl-6-(3-methylimidazol-4-yl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]-1-methylpyrrol-2-yl]-(4-methylpiperazin-1-yl)methanone
  参考文献：
  名称：

  Structure-based design of 2,6,7-trisubstituted-7H-pyrrolo[2,3-d]pyrimidines as Aurora kinases inhibitors

  摘要：

  This Letter reports the optimization of a pyrrolopyrimidine series as dual inhibitors of Aurora A/B kinases. This series derived from a pyrazolopyrimidine series previously reported as inhibitors of aurora kinases and CDKs. In an effort to improve the selectivity of this chemotype, we switched to the pyrrolopyrimidine core which allowed functionalization on C-2. In addition, the modeling rationale was based on superimposing the structures of Aurora-A kinase and CDK2 which revealed enough differences leading to a path for selectivity improvement. The synthesis of the new series of pyrrolopyrimidine analogs relied on the development of a different route for the two key intermediates 7 and 19 which led to analogs with both tunable activity against CDK1 and maintained cell potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.085
• 作为产物：
  描述：

  5-溴-2-氯-N-环戊基-4-嘧啶胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四丁基氟化铵 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-chloro-7-cyclopentyl-6-iodo-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Structure-based design of 2,6,7-trisubstituted-7H-pyrrolo[2,3-d]pyrimidines as Aurora kinases inhibitors

  摘要：

  This Letter reports the optimization of a pyrrolopyrimidine series as dual inhibitors of Aurora A/B kinases. This series derived from a pyrazolopyrimidine series previously reported as inhibitors of aurora kinases and CDKs. In an effort to improve the selectivity of this chemotype, we switched to the pyrrolopyrimidine core which allowed functionalization on C-2. In addition, the modeling rationale was based on superimposing the structures of Aurora-A kinase and CDK2 which revealed enough differences leading to a path for selectivity improvement. The synthesis of the new series of pyrrolopyrimidine analogs relied on the development of a different route for the two key intermediates 7 and 19 which led to analogs with both tunable activity against CDK1 and maintained cell potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.085

文献信息

• CDK9抑制剂及其制备方法与应用
  申请人：深圳湾实验室坪山生物医药研发转化中心

  公开号：CN112125911B

  公开（公告）日：2022-08-09

  本申请提供了一种CDK9抑制剂，CDK9抑制剂为嘧啶并吡咯类激酶抑制剂，且化学结构通式如式I所示：CDK9抑制剂为嘧啶并吡咯类激酶抑制剂，该嘧啶并吡咯类激酶所适应的蛋白靶点是丝氨酸/苏氨酸激酶CDK9，该CDK9抑制剂表现出较高的特异性以及较低的细胞毒性，提供了一种用于预防或治疗肿瘤生长与转移的对CDK9具有选择性的、毒副效果小、作用效果强的CDK9抑制剂，从而通过该抑制剂调控CDK9的生物学功能，抑制肿瘤的生长、增殖过程。