3-amino-N-phenyl-4-phenylaminobenzamide | 1268527-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-N-phenyl-4-phenylaminobenzamide
• 英文别名: 3-amino-4-anilino-N-phenylbenzamide
• CAS: 1268527-73-6
• 化学式: C₁₉H₁₇N₃O
• 分子量: 303.363
• InChiKey: HIPXKKACOFXILA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-N-phenyl-4-phenylaminobenzamide 在 manganese(IV) oxide 、 氯化锆(IV) 作用下， 以 乙醇 为溶剂， 反应 24.58h， 生成 3-ethyl-2-[(E)-2-(methylphenylamino)ethenyl]-1-phenyl-5-phenylcarbamoyl-1H-benzoimidazol-3-ium iodide
  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 在 palladium 10% on activated carbon 、 potassium carbonate 、 肼 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 8.5h， 生成 3-amino-N-phenyl-4-phenylaminobenzamide
  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

文献信息

• Cp2ZrCl2-catalyzed synthesis of 2-aminovinyl benzimidazoles under microwave conditions
  作者：Qi Sun、Cheng-Jun Wang、Shan-Shan Gong、Yong-Jian Ai、Hong-Bin Sun

  DOI：10.1016/j.cclet.2014.11.014

  日期：2015.3

  A microwave-assisted general method for the synthesis of 2-aminovinyl benzimidazoles has been developed. Treatment of the 1,2-phenylenediamines and N-arylated/N,N-diallcylated 3-aminoacroleins with bis(cyclopentadienyl)zirconium(IV) dichloride (Cp(2)ZECl(2)) as the catalyst under microwave irradiation for 3-5 min followed by in situ MnO2 oxidation afforded thirteen 2-aminovinyl benzimidazoles in good yields. (C) 2014 Qi Sun and Hong-Bin Sun. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.
• Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV
  作者：Qi Sun、Runzhi Wu、Sutang Cai、Yuan Lin、Llewlyn Sellers、Kaori Sakamoto、Biao He、Blake R. Peterson

  DOI：10.1021/jm100912b

  日期：2011.3.10

  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.