2,3-dihydro-2-(2,3-dimethoxyphenyl)quinazolin-4(1H)-one

• 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-dihydro-2-(2,3-dimethoxyphenyl)quinazolin-4(1H)-one
• 英文别名: 2-(2,3-dimethoxyphenyl)-2,3-dihydro-1H-quinazolin-4-one
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: BBVVUIHGZUCGGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-(2,3-dimethoxyphenyl)quinazolin-4(1H)-one 、 diphosphorus pentasulfide 、 吡啶 以50%的产率得到
  参考文献：
  名称：

  SHARMA, S. D.;KAUR, VERINDER, SYNTHESIS,(1989) N, C. 677-680

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯甲酰胺 、 2,3-二甲氧基苯甲醛 在 碘 作用下， 反应 1.0h， 以93%的产率得到2,3-dihydro-2-(2,3-dimethoxyphenyl)quinazolin-4(1H)-one
  参考文献：
  名称：

  [bmim+][ ]碘催化合成2-Arylquinazolin-4(3H)-one衍生物

  摘要：

  在室温或 80 °C 氮气氛下，控制芳香醛和 2-氨基苯甲酰胺在碘催化的离子液体中反应的选择性导致合成（E）-席夫碱、2,3-二氢-2-芳基喹唑啉-4(1H)-one 和 2-芳基喹唑啉-4(3H)-one 衍生物，产率极好。

  DOI：

  10.1080/00397910903318609

文献信息

• Synthesis of 2-Arylquinazolin-4(3<i>H</i>)-one Derivatives Catalyzed by Iodine in [bmim⁺][ ]
  作者：Xiang-Shan Wang、Ke Yang、Mei-Mei Zhang、Chang-Sheng Yao

  DOI：10.1080/00397910903318609

  日期：2010.8.5

  Controlling selectivity of the reactions of aromatic aldehydes and 2-aminobenzamide in ionic liquid catalyzed by iodine at either room temperature or at 80 °C under nitrogen resulted in the synthesis of (E)-Schiff bases, 2,3-dihydro-2-arylquinazolin-4(1H)-one and 2-arylquinazolin-4(3H)-one derivatives, in excellent yields.

  在室温或 80 °C 氮气氛下，控制芳香醛和 2-氨基苯甲酰胺在碘催化的离子液体中反应的选择性导致合成（E）-席夫碱、2,3-二氢-2-芳基喹唑啉-4(1H)-one 和 2-芳基喹唑啉-4(3H)-one 衍生物，产率极好。
• 6-Alkylamino- and 2,3-Dihydro-3‘-methoxy-2-phenyl-4-quinazolinones and Related Compounds:  Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization
  作者：Mann-Jen Hour、Li-Jiau Huang、Sheng-Chu Kuo、Yi Xia、Kenneth Bastow、Yuka Nakanishi、Ernest Hamel、Kuo-Hsiung Lee

  DOI：10.1021/jm000151c

  日期：2000.11.1

  As part of our continuing search for potential anticancer candidates among 2-phenyl-4-quinolones and 2-phenyl-4-quinazolinones, two series of 6,7,2',3',4',5'-substituted 2-phenyl-4-quinazolinones and 6,2',3',4',5'-substituted 2,3-dihydro-2-phenyl-4-quinazolinones were synthesized and evaluated for cytotoxicity and as inhibitors of tubulin polymerization. In general, a good correlation was found between the two activities. Five of the 6-substituted heterocyclic 2-phenyl-4-quinozolinones (37-51) showed significant cytotoxicity against a panel of human tumor cell lines with EC50 values in the low micromolar to nanomolar concentration ranges. Compound 38 was the most potent of these compounds, as well as the most potent inhibitor of tubulin polymerization in this series. The activity of 38 was in the same range as those of the antimitotic natural products, colchicine, podophyllotoxin, and combretastatin A-4. Substituted 2-phenyl-4-quinazolinones and 2,3-dihydro-2-phenyl-4-quinazolinones also displayed highly selective cytotoxicity against the ovarian cancer 1A9 and P-gp resistant KB-VIN cell lines.
• Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the presence of nanocomposites under microwave irradiation
  作者：Javad Safari、Soheila Gandomi-Ravandi

  DOI：10.1016/j.molcata.2014.02.013

  日期：2014.8

  The preparation of quinazolinones has been developed by the condensation of aromatic aldehydes and 2-aminobenzamide in the presence of transition metal-CNTs nanocomposites as novel and recyclable catalyst under microwave and solvent-free conditions. This methodology provides a high speed path for the green and mild synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones with high structural diversity. The present methodology has advantages such as high activity and reusability of catalysts, heterogeneous nature of catalysts, no use of hazardous organic solvents and green conditions. (C) 2014 Elsevier B.V. All rights reserved.
• SHARMA, S. D.;KAUR, VERINDER, SYNTHESIS,(1989) N, C. 677-680
  作者：SHARMA, S. D.、KAUR, VERINDER

  DOI：——

  日期：——
• US6479499B1
  申请人：——

  公开号：US6479499B1

  公开（公告）日：2002-11-12