N-(2-phenylquinazolin-4-yl)-benzene-1,4-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(2-phenylquinazolin-4-yl)-benzene-1,4-diamine
• 英文别名: 3-N-(2-phenylquinazolin-4-yl)benzene-1,3-diamine
• 化学式: C₂₀H₁₆N₄
• 分子量: 312.374
• InChiKey: NBXTWWGEAVMGBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 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：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-phenylquinazolin-4-yl)-benzene-1,4-diamine 、 2-氯噻吩-5-甲酸 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.66h， 以81%的产率得到5-chloro-N-(3-((2-phenylquinazolin-4-yl)amino)phenyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling insights of 2-arylquinazoline benzamide derivatives as anti-tubercular agents

  摘要：

  DOI：

  10.1016/j.molstruc.2020.128493
• 作为产物：
  描述：

  2-苯基-4-[3H]喹唑啉酮 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 12.0h， 生成 N-(2-phenylquinazolin-4-yl)-benzene-1,4-diamine
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling insights of 2-arylquinazoline benzamide derivatives as anti-tubercular agents

  摘要：

  DOI：

  10.1016/j.molstruc.2020.128493

文献信息

• Synthesis and SAR study of acridine, 2-methylquinoline and 2-phenylquinazoline analogues as anti-prion agents
  作者：H. Cope、R. Mutter、W. Heal、C. Pascoe、P. Brown、S. Pratt、B. Chen

  DOI：10.1016/j.ejmech.2006.05.002

  日期：2006.10

  Transmissible spongiform encephalopathies (TSEs) are thought to arise from aggregation of a protease resistant protein denoted PrPSc, which is a misfolded isoform of the normal cellular prion protein PrPC. Using virtual high-throughput screening we have selected structures analogous to acridine, 2-methyquinoline and 2-phenylquinazoline as potential therapeutic candidates for the treatment of TSEs. From the synthesis and screening of constructed libraries we have shown that an electron-rich aromatic ring attached through an amine linker to the position para to the ring nitrogen is beneficial to both binding to PrPC and the suppression of PrPSc accumulation for acridine and 2-methylquinoline analogues. 2-Phenylquinazoline analogues appear to utilise a different mode of action by binding at a different location and/or pose. We report IC(50)s in the nanomolar range. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Synthesis, biological evaluation and molecular modelling insights of 2-arylquinazoline benzamide derivatives as anti-tubercular agents
  作者：Satyaveni Malasala、Md Naiyaz Ahmad、Jitendra Gour、Manjulika Shukla、Grace Kaul、Abdul Akhir、Srikanth Gatadi、Y.V. Madhavi、Sidharth Chopra、Srinivas Nanduri

  DOI：10.1016/j.molstruc.2020.128493

  日期：2020.10