N-phenyl-4,5-bis(anilino)phthalimide | 130672-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-phenyl-4,5-bis(anilino)phthalimide
• 英文别名: 2-Phenyl-5,6-bis-phenylamino-isoindole-1,3-dione；5,6-dianilino-2-phenylisoindole-1,3-dione
• CAS: 130672-98-9
• 化学式: C₂₆H₁₉N₃O₂
• 分子量: 405.456
• InChiKey: LRCXLVSLCVACQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl 4,5-bis((trimethylsilyl)oxy)cyclohexa-1,4-dienedicarboxylate 、 苯胺 反应 12.0h， 以23%的产率得到N-phenyl-4,5-bis(anilino)phthalimide
  参考文献：
  名称：

  Matlin, Stephen A.; Barron, Kenneth, Journal of Chemical Research, Miniprint, 1990, # 8, p. 1920 - 1943

  摘要：

  DOI：

文献信息

• Dianilinophthalimides: Potent and Selective, ATP-Competitive Inhibitors of the EGF-Receptor Protein Tyrosine Kinase
  作者：Uwe Trinks、Elisabeth Buchdunger、Pascal Furet、Wilhelm Kump、Helmut Mett、Thomas Meyer、Marcel Mueller、Urs Regenass、Greti Rihs

  DOI：10.1021/jm00033a019

  日期：1994.4

  Dianilinophthalimides represent a novel class of inhibitors of the EGF-receptor protein tyrosine kinase with a high degree of selectivity versus other tyrosine and serine/threonine kinases. Steady-state kinetic analysis of compound 3, which showed potent inhibitory activity, revealed competitive type kinetics relative to ATP. Despite a highly symmetrical structure of compound 3, X-ray studies revealed an unsymmetrical propeller-shaped conformation of the molecule which differs clearly from that of the constitutionally related staurosporine aglycons. These conformational differences may explain the reversal of the selectivity profile of compound 3 relative to the staurosporine aglycons. In cellular assays compounds 3 and 4 have been shown to inhibit EGF-induced receptor autophosphorylation, c-fos induction and EGF-dependent proliferation of Balb/ c MK cells. This inhibition was selective as compounds had no effect on PDGF-induced receptor autophosphorylation and c-fos induction. Furthermore, compound 3 showed potent antitumor activity in vivo at well-tolerated doses.
• Trinks Uwe, Buchdunger Elisabeth, Furet Pascal, Kump Wilhelm, Mett Helmut+, J. Med. Chem, 37 (1994) N 7, S 1015-1027
  作者：Trinks Uwe, Buchdunger Elisabeth, Furet Pascal, Kump Wilhelm, Mett Helmut+

  DOI：——

  日期：——
• Matlin, Stephen A.; Barron, Kenneth, Journal of Chemical Research, Miniprint, 1990, # 8, p. 1920 - 1943
  作者：Matlin, Stephen A.、Barron, Kenneth

  DOI：——

  日期：——