(4-苯并恶唑-2-基-2-硝基苯基)苯胺 | 101884-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (4-苯并恶唑-2-基-2-硝基苯基)苯胺
• 英文名称: (4-benzooxazol-2-yl-2-nitrophenyl)phenylamine
• 英文别名: 4-(1,3-benzoxazol-2-yl)-2-nitro-N-phenylaniline
• CAS: 101884-49-5
• 化学式: C₁₉H₁₃N₃O₃
• 分子量: 331.331
• InChiKey: XPZPHZKODJEECX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-苯并恶唑-2-基-2-硝基苯基)苯胺 在 palladium 10% on activated carbon 、 氯化锆(IV) 、 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV

  摘要：

  Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with alpha,beta-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.

  DOI：

  10.1021/jm100912b
• 作为产物：
  描述：

  苯胺 、 2-(4-氯-3-硝基苯基)-1,3-苯并恶唑 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以84%的产率得到(4-苯并恶唑-2-基-2-硝基苯基)苯胺
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV

  摘要：

  Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with alpha,beta-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.

  DOI：

  10.1021/jm100912b