2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one | 63422-23-1

• 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-(3-hydroxy-4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(3-hydroxy-4-methoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one；2-(3-Hydroxy-4-methoxy-phenyl)-2,3-dihydro-1H-chinazolin-4-on；2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 63422-23-1
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: KMAFKCDKXJIKRB-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C(Solv: ethanol (64-17-5))
• 沸点：
  585.7±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-(3-(4-(2,6-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)isoxazol-5-yl)phenoxy)butoxy)-4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents

  摘要：

  A series of new 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydro quinazolinone hybrids with different linker architectures have been designed and synthesized. These compounds have been evaluated for their anticancer activity. One of the compounds 4c amongst this series has shown promising anticancer activity. Further some detailed biological assays relating to the cell cycle aspects and tubulin depolymerization activity have been examined with a view to understand the mechanism of action of this conjugate. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.004
• 作为产物：
  描述：

  N-(3-hydroxy-4-methoxy-benzyliden)-anthranilic acid amide 在 sodium hydroxide 作用下， 生成 2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  喹唑酮系列中的合成—VI：1：2：3：4-四氢-2-芳基-4-氧代喹唑啉的合成

  摘要：

  对N 2-芳基亚氨基甲酰胺的异构体变化的研究已导致合成了一系列新的1：2：3：4-四氢-4-氧代喹唑啉，通过氧化已从中获得了相应的喹唑-4-酮。基于本研究，2-（新合成ö氨基苯基）-3- ħ还报道-quinazol -4-酮（VI）。

  DOI：

  10.1016/0040-4020(57)85008-x

文献信息

• PEG-SO3H as Eco-friendly Polymeric Catalyst for the Synthesis of 2,3-Dihydroquinazolinones in Water
  作者：Guoli Huang、Bo Liu、Mingyu Teng、Yegao Chen

  DOI：10.2174/1570178613666160728101809

  日期：2016.9.21

  A facile, efficient, green, and environmentally benign method is described for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by direct cyclocondensation of 2-aminobenzamide with aldehydes or ketones in water using PEG-SO3H as an acidic catalyst under room temperature. This new method totally avoids the use of organic acids, toxic or expensive solvents and affording the corresponding product in good to excellent yields in this reaction.

  描述了一种简便、高效、绿色且对环境友好的方法，通过在室温下使用PEG-SO3H作为酸催化剂，将2-氨基苯胺与醛或酮在水中直接环缩合成2,3-二氢喹唑啉-4(1H)-酮。这种新方法完全避免了使用有机酸、毒性或昂贵的溶剂，并且在该反应中获得了良好至优异的产率。
• Mercuric chloride catalyzed synthesis of some anticancer 2-aryl-2,3-dihydroquinizolin-4(1H)-ones
  作者：Navudu Ramesh、Mannem Gangadhara Rao、Ravi Varala、V. Umamaheswra Rao、B. Hari Babu

  DOI：10.1007/s00044-016-1630-y

  日期：2016.9

  MDA-MB-231. Compounds 3b, 3c, 3d, 3e, and 3g showed significant total growth inhibition (TGI) values against the cell line MDA-MB-231 and compound 3j showed good TGI value against the cell line PANC 1. Compounds were also screened for their antibacterial activity and antioxidant activity by DPPH method.

  一系列10 2,3 - dihydroquinizolin-4（1 ħ）-酮衍生物，通过用在氯化汞催化量的存在下各种芳基醛（升汞邻氨基苯甲酰胺的乙醇介导的缩合合成2）。反应温度保持在60℃以得到良好的产物收率。该方法的重点包括使用实验室级的化学试剂作为试剂，并且易于后处理以获得高纯度的产品。在合成的十种衍生物中，三种化合物3f，3i和3j是新的，并评估了所有化合物对六种癌细胞系的细胞毒活性。化合物3b（IC50：26.1μgmL -1），3c（42.7μgmL -1）和3e（31.1μgmL -1）显示出对细胞系MDA-MB-231的活性。化合物3b，3c，3d，3e和3g对细胞系MDA-MB-231表现出显着的总生长抑制（TGI）值，化合物3j对细胞系PANC 1表现出良好的TGI值。 DPPH法测定其活性和抗氧化活性。
• Syntheses in the quinazolone series—VI
  作者：T.A. Kilroe Smith、Henry Stephen

  DOI：10.1016/0040-4020(57)85008-x

  日期：1957.1

  An investigation of the isomeric change of N2-arylideneorthanilamides has led to the synthesis of a new series of 1:2:3:4-tetrahydro-4-oxoquinazolines from which the corresponding quinazol-4-ones have been obtained by oxidation. Based on the present investigation, a new synthesis of 2-(o-aminophenyl)-3H-quinazol-4-one (VI) is also reported.

  对N 2-芳基亚氨基甲酰胺的异构体变化的研究已导致合成了一系列新的1：2：3：4-四氢-4-氧代喹唑啉，通过氧化已从中获得了相应的喹唑-4-酮。基于本研究，2-（新合成ö氨基苯基）-3- ħ还报道-quinazol -4-酮（VI）。
• Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents
  作者：Ahmed Kamal、E. Vijaya Bharathi、J. Surendranadha Reddy、M. Janaki Ramaiah、D. Dastagiri、M. Kashi Reddy、A. Viswanath、T. Lakshminarayan Reddy、T. Basha Shaik、S.N.C.V.L. Pushpavalli、Manika Pal Bhadra

  DOI：10.1016/j.ejmech.2010.12.004

  日期：2011.2

  A series of new 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydro quinazolinone hybrids with different linker architectures have been designed and synthesized. These compounds have been evaluated for their anticancer activity. One of the compounds 4c amongst this series has shown promising anticancer activity. Further some detailed biological assays relating to the cell cycle aspects and tubulin depolymerization activity have been examined with a view to understand the mechanism of action of this conjugate. (C) 2010 Elsevier Masson SAS. All rights reserved.