3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one | 192513-05-6

• 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-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 3-Hydroxy-2-(2-hydroxyphenyl)-1,2-dihydroquinazolin-4-one
• CAS: 192513-05-6
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: YWNTUOFSCXUWIK-UHFFFAOYSA-N

物化性质

• 沸点：
  458.0±55.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)
• 溶解度：
  >38.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 在 吡啶 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 1.0h， 以76%的产率得到二苯并[B,F][1,5]二氮杂辛因-6,12(5H,11H)-二酮
  参考文献：
  名称：

  3-羟基-1,2-二氢喹唑啉-4-酮与酰氯的反应

  摘要：

  3-羟基-1,2-二氢喹唑啉-4-酮与酰氯的反应可以得到不同类型的化合物。产物的结构取决于所用酰氯的类型和 3-羟基-1,2-二氢喹唑啉-4-one 的 2 位取代基的性质。

  DOI：

  10.1007/bf02495299
• 作为产物：
  描述：

  靛红酸酐 在 盐酸羟胺 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and antibiofilm evaluation of 3-hydroxy-2,3-dihydroquinazolin-4(1H)-one derivatives against opportunistic pathogen Acinetobacter baumannii

  摘要：

  The emergence of multidrug resistant microorganisms has triggered the impending need for new aitimicrobial strategies. The antivirulence strategy with the benefite of alleviating the drug resistance becomes the focus of research. In this study, 22 quorum sensing inhibitors were synthesized by mimicking the structure of autoinducer and acinetobactin and up to 34% biofilm inhibition was observed with 5u. The biofilm inhibition effect was further demonstrated with extracellular polysaccharides inhibition and synergism with Gentamycin sulphate.

  DOI：

  10.1016/j.bmc.2020.115606

文献信息

• Reactions of 3-hydroxy-1,2-dihydroquinazolin-4-ones with aldehydes
  作者：O. A. Luk'yanov、P. B. Gordeev

  DOI：10.1007/bf02641551

  日期：1998.12

  The reactions of 3-hydroxy-2-(2-hydroxyalkyl)- [or (2-hydroxyaryl)]-1-1,2-dihydroquinazolin-4-ones with formaldehyde or acetaldehyde afford 1,3-oxazino[3,4-a]quinazolin-4-one derivatives. The reactions with other aldehydes RCHO and 3-hydroxy-2-R'-1,2-dihydroquinazolin-4-ones can give 3-hydroxy-2-R-1,2-dihydroquinazolin-4-ones, 2-substituted quinazolin-4-ones, or dianthranilide.
• Reaction ofo-aminobenzohydroxamic acid with aldehydes
  作者：O. A. Luk'yanov、P. B. Gordeev

  DOI：10.1007/bf02495358

  日期：1997.1

  The reaction of sigma-aminobenzohydroxamic acid with aliphatic, aromatic, or heterocyclic aldehydes leads to the formation of derivatives of 3-hydroxy-1,2-dihydroquinazolin-4-one.
• Reactions of 3-hydroxy-1,2-dihydroquinazolin-4-ones with acid chlorides
  作者：O. A. Luk'yanov、P. B. Gordeev

  DOI：10.1007/bf02495299

  日期：1999.7

  The reactions of 3-hydroxy-1,2-dihydroquinazolin-4-ones with acid chlorides can afford compounds of different types. The structures of the products depend on the type of acid chloride used and on the nature of the substituent at position 2 of the 3-hydroxy-1,2-dihydroquinazolin-4-one.

  3-羟基-1,2-二氢喹唑啉-4-酮与酰氯的反应可以得到不同类型的化合物。产物的结构取决于所用酰氯的类型和 3-羟基-1,2-二氢喹唑啉-4-one 的 2 位取代基的性质。
• Synthesis and antibiofilm evaluation of 3-hydroxy-2,3-dihydroquinazolin-4(1H)-one derivatives against opportunistic pathogen Acinetobacter baumannii
  作者：Guo Yang、Cheng Cheng、Guo-Bo Xu、Lei Tang、Kim-Lee Chua、Yuan-Yong Yang

  DOI：10.1016/j.bmc.2020.115606

  日期：2020.8

  The emergence of multidrug resistant microorganisms has triggered the impending need for new aitimicrobial strategies. The antivirulence strategy with the benefite of alleviating the drug resistance becomes the focus of research. In this study, 22 quorum sensing inhibitors were synthesized by mimicking the structure of autoinducer and acinetobactin and up to 34% biofilm inhibition was observed with 5u. The biofilm inhibition effect was further demonstrated with extracellular polysaccharides inhibition and synergism with Gentamycin sulphate.