2-[(E)-2-(3-chlorophenyl)ethenyl]quinazolin-4(3H)-one | 1207435-79-7

• 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: 2-[(E)-2-(3-chlorophenyl)ethenyl]quinazolin-4(3H)-one
• 英文别名: 2-[(E)-2-(3-chlorophenyl)vinyl]quinazolin-4(3H)-one；2-((E)-2-(3-chloro-phenyl)-vinyl)-3H-quinazolin-4-one；2-[(E)-2-(3-chlorophenyl)ethenyl]-3H-quinazolin-4-one
• CAS: 1207435-79-7
• 化学式: C₁₆H₁₁ClN₂O
• 分子量: 282.729
• InChiKey: IRHYHGNDSSJFBV-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(3-chlorophenyl)ethenyl]quinazolin-4(3H)-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 88.0h， 生成 3-[[2-[(E)-2-(3-chlorophenyl)vinyl]quinazolin-4-yl]amino]phenol
  参考文献：
  名称：

  The p53 stabilizing agent CP-31398 and multi-kinase inhibitors. Designing, synthesizing and screening of styrylquinazoline series

  摘要：

  Quinazoline derivatives constitute a large family of small-molecule inhibitors of tyrosine kinases. In the current study, the p53 protein reactivator CP-31398 was tested against a panel of kinases on the assumption that it was structurally similar to other active inhibitors. Although it was found to be active in the enzyme-based assay, this compound did not block the proliferation of cancer cells at a feasible concentration level. The styrylquinazoline was used to design new structures that might be potential multitarget inhibitors. Subsequently, a series of compounds was obtained and characterized. Their inhibitory activity in a panel of tyrosine kinases had an antiproliferative effect against several cancer cell lines that have different expression levels of those proteins. The mode of protein interaction was tested for the most active compound in docking experiments. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.012
• 作为产物：
  描述：

  2-甲基-4(3H)-喹唑酮 、 3-氯苯甲醛 以93%的产率得到2-[(E)-2-(3-chlorophenyl)ethenyl]quinazolin-4(3H)-one
  参考文献：
  名称：

  Investigating Biological Activity Spectrum for Novel Styrylquinazoline Analogues

  摘要：

  本研究制备了一系列环取代的 2-苯乙烯基喹唑啉-4(3H)-酮和 4-氯-2-苯乙烯基喹唑啉衍生物。文中介绍了所讨论化合物的合成方法。化合物通过 RP-HPLC 进行分析，以确定其亲油性。测试了这些化合物对菠菜叶绿体光合电子传递（PET）的抑制活性。此外，还针对四种分枝杆菌菌株和八种真菌菌株对合成的化合物进行了体外初筛。一些化合物显示出与标准异烟肼相当或更高的生物活性。研究发现，R 取代基的电子特性，而不是化合物的总亲油性，对测试化合物的光合作用抑制活性起着决定性作用。

  DOI：

  10.3390/molecules14104246

文献信息

• Investigating Biological Activity Spectrum for Novel Styrylquinazoline Analogues
  作者：Josef Jampilek、Robert Musiol、Jacek Finster、Matus Pesko、James Carroll、Katarina Kralova、Marcela Vejsova、Jim O'Mahony、Aidan Coffey、Jiri Dohnal、Jaroslaw Polanski

  DOI：10.3390/molecules14104246

  日期：——

  In this study, series of ring-substituted 2-styrylquinazolin-4(3H)-one and 4-chloro-2-styrylquinazoline derivatives were prepared. The syntheses of the discussed compounds are presented. The compounds were analyzed by RP-HPLC to determine lipophilicity. They were tested for their inhibitory activity on photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial strains and against eight fungal strains. Several compounds showed biological activity comparable with or higher than that of the standard isoniazid. It was found that the electronic properties of the R substituent, and not the total lipophilicity of the compound, were decisive for the photosynthesis-inhibiting activity of tested compounds.

  本研究制备了一系列环取代的 2-苯乙烯基喹唑啉-4(3H)-酮和 4-氯-2-苯乙烯基喹唑啉衍生物。文中介绍了所讨论化合物的合成方法。化合物通过 RP-HPLC 进行分析，以确定其亲油性。测试了这些化合物对菠菜叶绿体光合电子传递（PET）的抑制活性。此外，还针对四种分枝杆菌菌株和八种真菌菌株对合成的化合物进行了体外初筛。一些化合物显示出与标准异烟肼相当或更高的生物活性。研究发现，R 取代基的电子特性，而不是化合物的总亲油性，对测试化合物的光合作用抑制活性起着决定性作用。
• Investigating the anti-proliferative activity of styrylazanaphthalenes and azanaphthalenediones
  作者：Anna Mrozek-Wilczkiewicz、Danuta S. Kalinowski、Robert Musiol、Jacek Finster、Agnieszka Szurko、Katarzyna Serafin、Magdalena Knas、Sishir K. Kamalapuram、Zaklina Kovacevic、Josef Jampilek、Alicja Ratuszna、Joanna Rzeszowska-Wolny、Des R. Richardson、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2010.02.025

  日期：2010.4

  A group of styrylazanaphthalenes and azanaphthalenediones were synthesized and tested for their anti-proliferative activity. Most of the compounds were obtained with the use of microwave-assisted synthesis. The lipophilicity of the compounds was measured by RP-HPLC and their anti-proliferative activity was assayed against the human SK-N-MC neuroepithelioma and HCT116 human colon carcinoma cell lines. Active compounds were also tested in clonogenity and comet assays. Several quinazolinone and styrylquinazoline analogues were found to have markedly greater anti-proliferative activity than desferoxamine and cis-platin. (C) 2010 Elsevier Ltd. All rights reserved.
• The p53 stabilizing agent CP-31398 and multi-kinase inhibitors. Designing, synthesizing and screening of styrylquinazoline series
  作者：Jacek Mularski、Katarzyna Malarz、Marcin Pacholczyk、Robert Musiol

  DOI：10.1016/j.ejmech.2018.12.012

  日期：2019.2

  Quinazoline derivatives constitute a large family of small-molecule inhibitors of tyrosine kinases. In the current study, the p53 protein reactivator CP-31398 was tested against a panel of kinases on the assumption that it was structurally similar to other active inhibitors. Although it was found to be active in the enzyme-based assay, this compound did not block the proliferation of cancer cells at a feasible concentration level. The styrylquinazoline was used to design new structures that might be potential multitarget inhibitors. Subsequently, a series of compounds was obtained and characterized. Their inhibitory activity in a panel of tyrosine kinases had an antiproliferative effect against several cancer cell lines that have different expression levels of those proteins. The mode of protein interaction was tested for the most active compound in docking experiments. (C) 2018 Elsevier Masson SAS. All rights reserved.