3-(2,4-dinitrophenylamino)-2-methylquinazoline-4(3H)-one | 326903-40-6

• 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: 3-(2,4-dinitrophenylamino)-2-methylquinazoline-4(3H)-one
• 英文别名: 3-(2,4-dinitrophenylamino)-2-methylquinazolin-4(3H)-one；3-(2,4-Dinitroanilino)-2-methylquinazolin-4-one
• CAS: 326903-40-6
• 化学式: C₁₅H₁₁N₅O₅
• 分子量: 341.283
• InChiKey: GWTNSACJUXJFHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 以 乙醇 为溶剂， 反应 12.16h， 生成 3-(2,4-dinitrophenylamino)-2-methylquinazoline-4(3H)-one
  参考文献：
  名称：

  Expeditious Synthesis and Spectroscopic Characterization of 2-Methyl-3-substituted-quinazolin-4(3H)-one Derivatives

  摘要：

  喹唉及其衍生物是一类因其治疗多样性和在药物设计和制药中的广泛应用而著名的生物活性杂环化合物。本研究通过将邻氨基苯甲酸转化为2-甲基-4H-3,1-苯并恶嗪-4-酮7，进而与一系列含有氨基的基团反应，合成了一系列2-甲基-3-取代喹唑啉-4(3H)-酮衍生物8a-q。通过选择溶剂和反应温度作为关键参数的精细反应优化研究，实现了无催化剂的合成路线。合成的化合物的化学结构通过IR、UV、1H-NMR、13C-NMR、DEPT-135以及分析数据进行了确认。

  DOI：

  10.13005/ojc/330203

文献信息

• An Efficient One-Pot Access to Quinazolinone Derivatives Using TiO2 Nanoparticles as Catalyst: Synthesis and Vasorelaxant Activity Evaluation
  作者：Ali Khalafi-Nezhad、Farhad Panahi、Saghar Haghighi、Azar Purkhosrow

  DOI：10.1055/s-0031-1290610

  日期：2012.4

  A variety of quinazolinone derivatives were successfully synthesized, via a three-component condensation reaction between anthranilic acid, acetic anhydride, and amines. This process was accomplished in the presence of catalytic amount of titanium dioxide nanoparticles (nano-TiO2), under solvent-free conditions. The synthesized compounds were evaluated for their vasorelaxant activity as they revealed a range of activities on the isolated thoracic rat aorta.

  成功合成了一系列奎嗪啉酮衍生物，通过对氨基苯甲酸、醋酸酐和胺类进行三组分缩合反应。在无溶剂条件下，使用催化量的二氧化钛纳米颗粒（nano-TiO2）完成该过程。合成的化合物被评估其血管舒张活性，因为它们在分离的胸部大鼠主动脉上表现出一系列活性。
• Expeditious Synthesis and Spectroscopic Characterization of 2-Methyl-3-substituted-quinazolin-4(3H)-one Derivatives
  作者：OLAYINKA O. AJANI、OLUWATOSIN Y. AUDU、MARKUS W. GERMANN、BABATUNDE L. BELLO

  DOI：10.13005/ojc/330203

  日期：2017.4.28

  Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.

  喹唉及其衍生物是一类因其治疗多样性和在药物设计和制药中的广泛应用而著名的生物活性杂环化合物。本研究通过将邻氨基苯甲酸转化为2-甲基-4H-3,1-苯并恶嗪-4-酮7，进而与一系列含有氨基的基团反应，合成了一系列2-甲基-3-取代喹唑啉-4(3H)-酮衍生物8a-q。通过选择溶剂和反应温度作为关键参数的精细反应优化研究，实现了无催化剂的合成路线。合成的化合物的化学结构通过IR、UV、1H-NMR、13C-NMR、DEPT-135以及分析数据进行了确认。