4-(4-Benzyl-1-piperazinyl)-2-phenylquinazoline

• 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: 4-(4-Benzyl-1-piperazinyl)-2-phenylquinazoline
• 英文别名: 4-(4-benzylpiperazin-1-yl)-2-phenylquinazoline
• 化学式: C₂₅H₂₄N₄
• 分子量: 380.492
• InChiKey: XATVSLHMOONKQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯-2-苯基喹唑啉 在 盐酸 、 三乙酰氧基硼氢化钠 、 potassium carbonate 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-(4-Benzyl-1-piperazinyl)-2-phenylquinazoline
  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

• Design, Synthesis, and Biological Investigation of Quinazoline Derivatives as Multitargeting Therapeutics in Alzheimer’s Disease Therapy
  作者：Akash Verma、Digambar Kumar Waiker、Neha Singh、Anima Roy、Namrata Singh、Poorvi Saraf、Bhagwati Bhardwaj、Sairam Krishnamurthy、Surendra Kumar Trigun、Sushant Kumar Shrivastava

  DOI：10.1021/acschemneuro.3c00653

  日期：2024.2.21

  An efficient and promising method of treating complex neurodegenerative diseases like Alzheimer’s disease (AD) is the multitarget-directed approach. Here in this work, a series of quinazoline derivatives (AV-1 to AV-21) were rationally designed, synthesized, and biologically evaluated as multitargeted directed ligands against human cholinesterase (hChE) and human β-secretase (hBACE-1) that exhibit

  治疗阿尔茨海默病（AD）等复杂神经退行性疾病的一种有效且有前景的方法是多靶点定向方法。在这项工作中，一系列喹唑啉衍生物（ AV-1至AV-21 ）被合理设计、合成并进行生物学评估，作为针对人胆碱酯酶（hChE）和人β-分泌酶（hBACE-1）的多靶点定向配体，其表现出中度至良好的抑制作用。该系列的化合物AV-1 、 AV-2和AV-3对这些靶点表现出平衡且显着的抑制作用。通过 PAMPA-BBB 测定，这些化合物还表现出优异的血脑屏障渗透性。化合物AV-2显着取代乙酰胆碱酯酶外周阴离子位点 (AChE-PAS) 的碘化丙啶 (PI)，并且发现在最大测试浓度 (80 μM) 下对分化的 SH-SY5Y 细胞系无神经毒性。在硫黄素 T 测定中，化合物AV-2还可以阻止 AChE 和自身诱导的 Aβ 聚集。此外，在体内行为 Y 迷宫和莫里斯水迷宫研究中，化合物AV-2分别显着改善东莨菪碱和 Aβ
• US7345045B2
  申请人：——

  公开号：US7345045B2

  公开（公告）日：2008-03-18
• 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.