5-benzyl-2-(4-(3-nitrobenzyl)piperazin-1-yl)pyrimidine | 1283119-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-benzyl-2-(4-(3-nitrobenzyl)piperazin-1-yl)pyrimidine
• 英文别名: 5-Benzyl-2-[4-[(3-nitrophenyl)methyl]piperazin-1-yl]pyrimidine
• CAS: 1283119-43-6
• 化学式: C₂₂H₂₃N₅O₂
• 分子量: 389.457
• InChiKey: RHRHDFUNOHEZRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzyl-2-(4-(3-nitrobenzyl)piperazin-1-yl)pyrimidine 在 10% palladium on activated charcoal 、 氢气 作用下， 生成 5-benzyl-2-(piperazin-1-yl)pyrimidine
  参考文献：
  名称：

  Anti-tumor pyrimidinylpiperazines bind to the prosurvival Bcl-2 protein family member Bcl-XL

  摘要：

  Overexpression of prosurvival or underexpression of pro-death Bcl-2 family proteins can lead to cancer cell resistance to chemotherapy and radiation treatment. Inhibition of the prosurvival Bcl-2 family proteins has become a strategy for cancer therapy and inhibitors are currently being evaluated in the clinic both as single agents and in combination with established drugs. Here we describe the design, synthesis, and evaluation of pyrimidylpiperazines that were discovered to be inhibitors of the prosurvival Bcl-2 protein family member Bcl-XL. This study identified compound 21 which demonstrated a GI(50) value of 8.4 mu M against A549 lung adenocarcinoma cells and a binding affinity K-i value for Bcl-XL of 127 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.054
• 作为产物：
  描述：

  B-苄基-9-硼杂双环[3.3.1]壬烷 在 盐酸 、 四(三苯基膦)钯 、 三乙酰氧基硼氢化钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 5-benzyl-2-(4-(3-nitrobenzyl)piperazin-1-yl)pyrimidine
  参考文献：
  名称：

  Anti-tumor pyrimidinylpiperazines bind to the prosurvival Bcl-2 protein family member Bcl-XL

  摘要：

  Overexpression of prosurvival or underexpression of pro-death Bcl-2 family proteins can lead to cancer cell resistance to chemotherapy and radiation treatment. Inhibition of the prosurvival Bcl-2 family proteins has become a strategy for cancer therapy and inhibitors are currently being evaluated in the clinic both as single agents and in combination with established drugs. Here we describe the design, synthesis, and evaluation of pyrimidylpiperazines that were discovered to be inhibitors of the prosurvival Bcl-2 protein family member Bcl-XL. This study identified compound 21 which demonstrated a GI(50) value of 8.4 mu M against A549 lung adenocarcinoma cells and a binding affinity K-i value for Bcl-XL of 127 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.054