N-[2-(1,3-benzodioxol-5-yl)ethyl]-2-phenylquinazolin-4-amine | 1417558-45-2

• 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-(1,3-benzodioxol-5-yl)ethyl]-2-phenylquinazolin-4-amine
• CAS: 1417558-45-2
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: ZUTWKSLFARNSFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯-2-苯基喹唑啉 、 3,4-亚甲二氧基苯乙胺 在 三乙胺 作用下， 以 异丙醇 为溶剂， 以38.3%的产率得到N-[2-(1,3-benzodioxol-5-yl)ethyl]-2-phenylquinazolin-4-amine
  参考文献：
  名称：

  Molecular docking and synthesis of novel quinazoline analogues as inhibitors of transcription factors NF-κB activation and their anti-cancer activities

  摘要：

  NF-kappa B is a transcription factor protein complex that can be found in almost all animal cell types and is a key player in some cancers and inflammatory responses. It can enhance the proliferation rate, reduce apoptosis, as well as creating more blood flow to ensure the survival of cancer, thus blocking the NF-kappa B pathway has potential therapeutic benefit. We designed a series of compounds based on a quinazoline scaffold pharmacophore model which may have high binding affinity with the p50 subunit of NF-kappa B. The compound series with phenyl substitution at the 2 position of the quinazoline proved to be more effective at inhibiting NF-kappa B function both theoretically and experimentally. These compounds also reduce the proliferation of numerous tumor cell lines and the mean GI(50) for compound 2a is 2.88 mu M against the NCI-60 cell line. At the same time, compound 2a can induce significant apoptosis in EKVX cell line at the concentration of 1 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.051

文献信息

• Molecular docking and synthesis of novel quinazoline analogues as inhibitors of transcription factors NF-κB activation and their anti-cancer activities
  作者：Lu Xu、Wade A. Russu

  DOI：10.1016/j.bmc.2012.10.051

  日期：2013.1

  NF-kappa B is a transcription factor protein complex that can be found in almost all animal cell types and is a key player in some cancers and inflammatory responses. It can enhance the proliferation rate, reduce apoptosis, as well as creating more blood flow to ensure the survival of cancer, thus blocking the NF-kappa B pathway has potential therapeutic benefit. We designed a series of compounds based on a quinazoline scaffold pharmacophore model which may have high binding affinity with the p50 subunit of NF-kappa B. The compound series with phenyl substitution at the 2 position of the quinazoline proved to be more effective at inhibiting NF-kappa B function both theoretically and experimentally. These compounds also reduce the proliferation of numerous tumor cell lines and the mean GI(50) for compound 2a is 2.88 mu M against the NCI-60 cell line. At the same time, compound 2a can induce significant apoptosis in EKVX cell line at the concentration of 1 mu M. (C) 2012 Elsevier Ltd. All rights reserved.