N-(4-fluorobenzyl)-6-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine | 1637569-25-5

• 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: N-(4-fluorobenzyl)-6-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS: 1637569-25-5
• 化学式: C₁₃H₁₀FIN₄
• 分子量: 368.152
• InChiKey: XNRVAMQTQXXBIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  53.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-氯吡咯并嘧啶 在 甲醇 、 sodium hydroxide 、 sodium t-butanolate 、 lithium diisopropyl amide 作用下， 以 正丁醇 为溶剂， 生成 N-(4-fluorobenzyl)-6-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Identification of new 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines as highly potent EGFR-TK inhibitors with Src-family activity

  摘要：

  The epidermal growth factor receptor is an important target in molecular cancer therapy. Herein, the enzymatic inhibition potential of a series of chiral and non chiral pyrrolopyrimidine based derivatives have been investigated and optimised. Overall, seven new compounds were identified having enzymatic IC50 values comparable to or better than the commercial drug Erlotinib. High activity was also confirmed towards the epidermal growth factor receptor L858R and L861Q mutants. Based on calculated druglike properties, eight compounds were further evaluated towards a panel of 52 other kinases revealing interesting Src-family kinase and colony stimulating factor 1 receptor kinase inhibitory activity. Cell proliferation studies with the cell lines A431, C-33A, AU-565, K-562 and genetically engineered Ba/F3-EGFRL858R cells also showed several molecules to be more active than Erlotinib, and thus confirming these pyrrolopyrimidines as attractive drug candidates or lead structures. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2014.04.011