2-[(4-Quinazolin-4-ylpiperazin-1-yl)methyl]phenol | 1417558-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-[(4-Quinazolin-4-ylpiperazin-1-yl)methyl]phenol
• 英文别名: 2-[(4-quinazolin-4-ylpiperazin-1-yl)methyl]phenol
• CAS: 1417558-52-1
• 化学式: C₁₉H₂₀N₄O
• 分子量: 320.394
• InChiKey: PWMOQKSUXLFNPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(quinazolin-4-yl)piperazine-1-carboxylate 在 盐酸 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 2-[(4-Quinazolin-4-ylpiperazin-1-yl)methyl]phenol
  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.