ethyl 2-{2-[(4-cyclohexylbenzyl)amino]-6-(4-nitrophenoxy)-9H-purin-9-yl}acetate | 1449781-66-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-{2-[(4-cyclohexylbenzyl)amino]-6-(4-nitrophenoxy)-9H-purin-9-yl}acetate
• 英文别名: Ethyl 2-[2-[(4-cyclohexylphenyl)methylamino]-6-(4-nitrophenoxy)purin-9-yl]acetate；ethyl 2-[2-[(4-cyclohexylphenyl)methylamino]-6-(4-nitrophenoxy)purin-9-yl]acetate
• CAS: 1449781-66-1
• 化学式: C₂₈H₃₀N₆O₅
• 分子量: 530.583
• InChiKey: OBEUJENJUOHVIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2-{2-[(4-cyclohexylbenzyl)amino]-6-(4-nitrophenoxy)-9H-purin-9-yl}acetate 在 水 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 acetoxymethyl 2-{2-[(4-cyclohexylbenzyl)amino]-6-(4-nitrophenoxy)-9H-purin-9-yl}acetate
  参考文献：
  名称：

  A 2,6,9-hetero-trisubstituted purine inhibitor exhibits potent biological effects against multiple myeloma cells

  摘要：

  A focused library of hetero-trisubstituted purines was developed for improving the cell penetrating and biological efficacy of a series of anti-Stat3 protein inhibitors. From this SAR study, lead agent 22e was identified as being a promising inhibitor of MM tumour cells (IC50's <5 mu M). Surprisingly, biophysical and biochemical characterization proved that 22e was not a Stat3 inhibitor. Initial screening against the kinome, prompted by the purine scaffold's history for targeting ATP binding pockets, suggests possible targeting of the JAK family kinases, as well for ABL1 (nonphosphorylated F317L) and AAK1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.080
• 作为产物：
  描述：

  ethyl 2-{2-[(tert-butoxycarbonyl)(4-cyclohexylbenzyl)amino]-6-chloro-9H-purin-9-yl}acetate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 ethyl 2-{2-[(4-cyclohexylbenzyl)amino]-6-(4-nitrophenoxy)-9H-purin-9-yl}acetate
  参考文献：
  名称：

  A 2,6,9-hetero-trisubstituted purine inhibitor exhibits potent biological effects against multiple myeloma cells

  摘要：

  A focused library of hetero-trisubstituted purines was developed for improving the cell penetrating and biological efficacy of a series of anti-Stat3 protein inhibitors. From this SAR study, lead agent 22e was identified as being a promising inhibitor of MM tumour cells (IC50's <5 mu M). Surprisingly, biophysical and biochemical characterization proved that 22e was not a Stat3 inhibitor. Initial screening against the kinome, prompted by the purine scaffold's history for targeting ATP binding pockets, suggests possible targeting of the JAK family kinases, as well for ABL1 (nonphosphorylated F317L) and AAK1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.080