3-[4-(1-amino-2,4-dicyanopyrido[1,2-a]benzimidazol-3-yl)phenyl]propanoic acid | 1314881-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[4-(1-amino-2,4-dicyanopyrido[1,2-a]benzimidazol-3-yl)phenyl]propanoic acid
• 英文别名: 3-(4-(1-Amino-2,4-dicyanobenzo[4,5]imidazo[1,2-a]pyridin-3-yl)phenyl)propanoic acid
• CAS: 1314881-75-8
• 化学式: C₂₂H₁₅N₅O₂
• 分子量: 381.393
• InChiKey: VNBMLJZERKNHBR-UHFFFAOYSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[4-(1-amino-2,4-dicyanopyrido[1,2-a]benzimidazol-3-yl)phenyl]propanoic acid 、 甲胺 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 1.0h， 以23%的产率得到3-[4-(1-amino-2,4-dicyanopyrido[1,2-a]benzimidazol-3-yl)phenyl]-N-methylpropanamide
  参考文献：
  名称：

  Inhibition of the cellular function of perforin by 1-amino-2,4-dicyanopyrido[1,2-a]benzimidazoles

  摘要：

  A high throughput screen showed the ability of a 1-amino-2,4-dicyanopyrido[1,2-a]benzimidazole analogue to directly inhibit the lytic activity of the pore-forming protein perforin. A series of analogues were prepared to study structure-activity relationships (SAR) for the this activity, either directly added to cells or released in situ by KHYG-1 NK cells, at non-toxic concentrations. These studies showed that the pyridobenzimidazole moiety was required for effective activity, with strongly basic centres disfavoured. This class of compounds was relatively unaffected by the addition of serum, which was not the case for a previous class of direct inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.013
• 作为产物：
  描述：

  3-(4-甲酰基苯基)丙酸乙酯 在 哌啶 、 乙醇 、 sodium hydroxide 、 β-丙氨酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 3-[4-(1-amino-2,4-dicyanopyrido[1,2-a]benzimidazol-3-yl)phenyl]propanoic acid
  参考文献：
  名称：

  Inhibition of the cellular function of perforin by 1-amino-2,4-dicyanopyrido[1,2-a]benzimidazoles

  摘要：

  A high throughput screen showed the ability of a 1-amino-2,4-dicyanopyrido[1,2-a]benzimidazole analogue to directly inhibit the lytic activity of the pore-forming protein perforin. A series of analogues were prepared to study structure-activity relationships (SAR) for the this activity, either directly added to cells or released in situ by KHYG-1 NK cells, at non-toxic concentrations. These studies showed that the pyridobenzimidazole moiety was required for effective activity, with strongly basic centres disfavoured. This class of compounds was relatively unaffected by the addition of serum, which was not the case for a previous class of direct inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.013