N(4)-(4-chlorophenyl)-6-(1-naphthylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine | 1356907-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N(4)-(4-chlorophenyl)-6-(1-naphthylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
• 英文别名: 4-N-(4-chlorophenyl)-6-(naphthalen-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
• CAS: 1356907-54-4
• 化学式: C₂₃H₁₈ClN₅
• 分子量: 399.882
• InChiKey: XSIGGCHYNXSJBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  79.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氯苯胺 、 2-amino-4-chloro-6-(1-naphthylmethyl)-pyrrolo[2,3-d]pyrimidine 在 盐酸 、 ammonium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 12.0h， 以68%的产率得到N(4)-(4-chlorophenyl)-6-(1-naphthylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
  参考文献：
  名称：

  N4-Aryl-6-substitutedphenylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines as receptor tyrosine kinase inhibitors

  摘要：

  Six novel N-4-substitutedphenyl-6-substitutedphenylmethy1-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines were synthesized as multiple receptor tyrosine kinase (RTK) inhibitors and antitumor agents. An improvement in the inhibitory potency against epidermal growth factor receptor (EGFR), vascular endothelial growth factor receptor 1 (VEGFR-1) and vascular endothelial growth factor receptor 2 (VEGFR-2) assays and in the A431 cellular proliferation assay was observed for compounds 8-13 over the previously reported 5-7. Three compounds (8.9 and 13) demonstrated potent, multiple RTK inhibition and were more potent or equipotent compared to the lead compounds 5 and 7 and the standard compounds. Compounds 10 and 12 showed potent inhibition of VEGFR-2 over EGFR, platelet-derived growth factor receptor-p (PDGFR-p) and VEGFR-1. The results indicate that the RIM inhibitory profile could be modulated with slight variations to the N-4-aryl-6-substitutedphenylmethyl-7H-Pyrrolo[2,3-d]wrimidine-2,4-diamino scaffold. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.058

文献信息

• N4-Aryl-6-substitutedphenylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines as receptor tyrosine kinase inhibitors
  作者：Aleem Gangjee、Sonali Kurup、Michael A. Ihnat、Jessica E. Thorpe、Bryan Disch

  DOI：10.1016/j.bmc.2011.11.058

  日期：2012.1

  Six novel N-4-substitutedphenyl-6-substitutedphenylmethy1-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines were synthesized as multiple receptor tyrosine kinase (RTK) inhibitors and antitumor agents. An improvement in the inhibitory potency against epidermal growth factor receptor (EGFR), vascular endothelial growth factor receptor 1 (VEGFR-1) and vascular endothelial growth factor receptor 2 (VEGFR-2) assays and in the A431 cellular proliferation assay was observed for compounds 8-13 over the previously reported 5-7. Three compounds (8.9 and 13) demonstrated potent, multiple RTK inhibition and were more potent or equipotent compared to the lead compounds 5 and 7 and the standard compounds. Compounds 10 and 12 showed potent inhibition of VEGFR-2 over EGFR, platelet-derived growth factor receptor-p (PDGFR-p) and VEGFR-1. The results indicate that the RIM inhibitory profile could be modulated with slight variations to the N-4-aryl-6-substitutedphenylmethyl-7H-Pyrrolo[2,3-d]wrimidine-2,4-diamino scaffold. (C) 2011 Elsevier Ltd. All rights reserved.