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 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones catalyzed by graphene oxide nanosheets in an aqueous medium: “on-water” synthesis accompanied by carbocatalysis and selective C–C bond cleavage
  作者：Nazia Kausar、Indranil Roy、Dipankar Chattopadhyay、Asish R. Das

  DOI：10.1039/c6ra00388e

  日期：——

  Graphene oxide (GO) nanosheet catalyzed new and straightforward strategies for the construction of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones starting from anthranilamide (2-aminobenzamide) and an aldehyde/ketone in aqueous medium at room temperature have been realized. This catalyst is also found to be efficient for the expedient construction of quinazolin-4(3H)-ones starting from anthranilamide

  氧化石墨烯（GO）纳米片催化了在室温下在水性介质中从邻氨基苯甲酰胺（2-氨基苯甲酰胺）和醛/酮开始构建2,3-二氢喹唑啉酮和quinazolin-4（3 H）-ones的新的直接策略被实现。还发现这种催化剂对于从蒽酰胺和β-酮酸酯/ 1,3-二酮类化合物中选择性地进行CC键裂解β-酮酸酯/ 1之后的喹唑啉-4（3 H）-酮的便捷构造是有效的，3-二酮在高温下在无金属和无氧化剂的条件下。
• 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.
• US6479499B1
  申请人：——

  公开号：US6479499B1

  公开（公告）日：2002-11-12