1-amino-3-(4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-2,4-dicarbonitrile | 296244-60-5

• 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: 1-amino-3-(4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-2,4-dicarbonitrile
• 英文别名: 1-Amino-2-cyano-3-(4-hydroxyphenyl)pyrido[1,2-a][1,3]benzimidazol-4-yl cyanide
• CAS: 296244-60-5
• 化学式: C₁₉H₁₁N₅O
• mdl: MFCD00632805
• 分子量: 325.329
• InChiKey: DMVRZVGBLGRJRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-amino-3-(4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-2,4-dicarbonitrile 在 四丁基氟化铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-amino-3-[4-(2-hydroxyethoxy)phenyl]pyrido[1,2-a]benzimidazole-2,4-dicarbonitrile
  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：

  2-氰甲基苯并咪唑 、 4-羟基苯亚甲基丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以7%的产率得到1-amino-3-(4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-2,4-dicarbonitrile
  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

文献信息

• SPECIFIC INHIBITORS OF PROTEIN P21 AS THERAPEUTIC AGENTS
  申请人：BADEN-WÜRTTEMBERG STIFTUNG GMBH

  公开号：US20150210717A1

  公开（公告）日：2015-07-30

  The present invention relates to novel inhibitors of p21. These inhibitors are useful as therapeutic agents for promot ing cell regeneration and in the treatment of cancer. Improvement of cell regeneration is particularly desirable in patients of old age or in patients suffering from chronic diseases, acute or chronic injuries.
• [EN] SPECIFIC INHIBITORS OF PROTEIN P21 AS THERAPEUTIC AGENTS<br/>[FR] INHIBITEURS SPÉCIFIQUES DE LA PROTÉINE P21 COMME AGENTS THÉRAPEUTIQUES
  申请人：BADEN WUERTTEMBERG STIFTUNG GMBH

  公开号：WO2014041125A1

  公开（公告）日：2014-03-20

  The present invention relates to novel inhibitors of p21. These inhibitors are useful as therapeutic agents for promoting cell regeneration and in the treatment of cancer. Improvement of cell regeneration is particularly desirable in patients of old age or in patients suffering from chronic diseases, acute or chronic injuries.
• Inhibition of the cellular function of perforin by 1-amino-2,4-dicyanopyrido[1,2-a]benzimidazoles
  作者：Dani M. Lyons、Kristiina M. Huttunen、Kylie A. Browne、Annette Ciccone、Joseph A. Trapani、William A. Denny、Julie A. Spicer

  DOI：10.1016/j.bmc.2011.05.013

  日期：2011.7

  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.