(E)-2-styrylquinazolin-4(3H)-one | 53905-19-4

• 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: (E)-2-styrylquinazolin-4(3H)-one
• 英文别名: 2-Styrylquinazolin-4(3H)-one；2-[(E)-2-phenylethenyl]-3H-quinazolin-4-one
• CAS: 53905-19-4
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: JDEJRLXMWUYMSS-ZHACJKMWSA-N

物化性质

• 熔点：
  250-252 °C(Solv: 1,4-dioxane (123-91-1); water (7732-18-5); N,N-dimethylformamide (68-12-2))
• 沸点：
  434.9±38.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-styrylquinazolin-4(3H)-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 3.0h， 以81%的产率得到4-chloro-2-((E)-styryl)-quinazoline
  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
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 苯 为溶剂， 反应 21.0h， 生成 (E)-2-styrylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization

  摘要：

  A novel series of 2-styrylquinazolin-4(3H-ones which inhibited tubulin polymerization and the growth of L1210 murine leukemia cells was discovered. Extensive structure-activity relationship studies suggest that the entire quinazolinone structure was required, but activity was further enhanced by halide or small hydrophobic substituents at position 6. These analogues did not substantially interfere with the binding of radiolabeled colchicine, vinblastine, or GTP to tubulin and weakly stimulated GTP hydrolysis uncoupled from polymerization. Several analogues have shown in vivo tumor growth inhibitory activity in the L1210 leukemia model, with the lead compound 5o exhibiting good antitumor activity against murine solid tumors as well as human tumor xenografts.

  DOI：

  10.1021/jm00168a029

文献信息

• A Facile Microwave and SnCl2 Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
  作者：Nicholas S. O'Brien、Adam McCluskey

  DOI：10.1071/ch20101

  日期：——

  An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1 % SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17–99 %. This process was highly tolerant

  据报道，具有生物学重要性的支架2，3-二氢喹唑啉-4（1 H）-ones是一种优雅，简单，轻便且健壮的方法。1％SnCl 2催化/微波介导的方法提供了纯净的物质，在120°C的微波照射20分钟后通过冷却和过滤收集。总共制备了41种类似物，分离产率为17–99％。该过程对脂肪族，芳香族，杂环和无环醛具有很高的耐受性，但是呋喃，吡咯和噻吩醛的反应性与亲电子加成和/或Diels-Alder加成的倾向相关。结果，噻吩提供了高产率（80％），而吡咯羧醛没有反应。具有简单的肉桂醛，并在SbCl 3中介导的反应，并与α，β-不饱和醛等价的喹唑啉-4（3 H）-一个，而不是2,3-二氢喹唑啉-4（1 H）-一个。
• Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs
  作者：Dinesh Kumar、Pradeep S. Jadhavar、Manesh Nautiyal、Himanshu Sharma、Prahlad K. Meena、Legesse Adane、Sahaj Pancholia、Asit K. Chakraborti

  DOI：10.1039/c5ra03888j

  日期：——

  Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions.

  已开发出简单、方便且绿色的合成方案，用于在无催化剂和溶剂的条件下一锅法合成2,3-二取代喹唑啉-4(3H)-酮和2-苯乙烯基-3-取代喹唑啉-4(3H)-酮。
• Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
  作者：Zongbo Xie、Jin Lan、Haibo Zhu、Gaoyi Lei、Guofang Jiang、Zhanggao Le

  DOI：10.1016/j.cclet.2020.09.059

  日期：2021.4

  aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously

  已经开发了一种从各种氨基苯甲酰胺和原位生成的醛构建喹唑啉酮的简便串联途径。发现可见光起着双重作用：首先将醇氧化成醛，然后促进其与邻苯二甲酸的环化。取代的苯胺。此外，醇是醛的完美替代品，因为它们比醛更绿色，更易得，更经济，更稳定且毒性更低。第一反应步骤连续地为第二步骤提供材料，该材料有效地减少了由于醛的挥发，氧化和聚合而造成的损失，同时避免了其毒性。可以在可见光存在下制备各种喹唑啉酮，而无需任何其他光催化剂。发达的合成方案具有温和条件，广泛的底物范围，操作简便和高原子效率的优点，并在无金属，无光催化剂和环境条件下具有生态能源。
• Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I₂-mediated oxidative C–N bond formation
  作者：Xianhai Tian、Lina Song、Ertong Li、Qiang Wang、Wenquan Yu、Junbiao Chang

  DOI：10.1039/c5ra11262a

  日期：——

  A one-pot I2-mediated annulation reaction of substrates containing diamino groups and aldehydes has been developed via oxidative C–N bond formation. This general and environmentally benign synthetic approach provides facile access to a variety of 1,3-diazaheterocyclic compounds, including quinazolinones, benzimidazoles, and cyclic amidines.

  含二氨基和醛的底物的一锅I 2介导的环化反应是通过氧化C–N键形成的。这种通用且对环境无害的合成方法可轻松获得各种1,3-二氮杂杂环化合物，包括喹唑啉酮，苯并咪唑和环状am。
• Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
  作者：Subrata Sahoo、Shantanu Pal

  DOI：10.1021/acs.joc.1c02343

  日期：2021.12.17

  A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile

  首次通过铜催化的腈形成、水解和还原在一个锅中揭示了一种从 2-硝基苯甲醛构建喹唑啉酮的新型、高效和原子经济的方法。在该反应中，尿素用作生成腈的氮源，水合肼用于硝基的还原和腈的水解，大气中的氧气用作唯一的氧化剂。该方法描绘了具有良好官能团耐受性的宽底物范围。此外，该方法还用于合成裂殖菌素、色胺菊酯、phaitanthrin-A、phaitanthrin-B和8 H-喹唑啉[4,3 - b ]quinazolin-8-one。