3-[2-(3,4-二甲氧基苯基)乙基]喹唑啉-4-酮 | 62787-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-[2-(3,4-二甲氧基苯基)乙基]喹唑啉-4-酮
• 英文名称: 3-(3,4-dimethoxyphenethyl)quinazolin-4(3H)-one
• 英文别名: 3-[2-(3,4-Dimethoxyphenyl)ethyl]quinazolin-4-one
• CAS: 62787-40-0
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: DGDNNUVSGKDIOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 iron(II) sulfate 作用下， 以 水 、 苯 为溶剂， 反应 16.75h， 生成 3-[2-(3,4-二甲氧基苯基)乙基]喹唑啉-4-酮
  参考文献：
  名称：

  Joshi; Chaudhari; Mogera, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 5, p. 431 - 434

  摘要：

  DOI：

文献信息

• Synthesis, Anti-microbial and Molecular Docking Studies of Quinazolin-4(3H)-one Derivatives
  作者：Yahia Mabkhot、Munirah Al-Har、Assem Barakat、Fahad Aldawsari、Ali Aldalbahi、Zaheer Ul-Haq

  DOI：10.3390/molecules19078725

  日期：——

  In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a–h and 3a–d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6 ± 0.5, 24.3 ± 0.4, 30.1 ± 0.6, and 25.1 ± 0.5 µg/mL against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3 ± 0.6, 23.1 ± 0.4, and 26.1 ± 0. 5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.

  在这项工作中，描述了一些新的取代喹唑啉酮2a–h和3a–d的合成、抗微生物活性及分子对接研究。从2-氨基苯甲酰胺衍生物1出发，通过微波辅助和经典方法，高效合成了一系列喹唑啉酮衍生物。其中一些取代喹唑啉酮通过琼脂孔扩散法测试了它们对革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）以及抗真菌活性（烟曲霉、酿酒酵母和白色念珠菌）的抗微生物活性。在制备的产品中，3-苄基-2-(4-氯苯基)喹唑啉-4(3H)-酮（3a）表现出最强的体外抗微生物活性，对金黄色葡萄球菌、枯草芽孢杆菌、铜绿假单胞菌和大肠杆菌的MIC值分别为25.6 ± 0.5、24.3 ± 0.4、30.1 ± 0.6和25.1 ± 0.5 µg/mL。化合物3a还表现出最强的体外抗真菌活性，对烟曲霉、酿酒酵母和白色念珠菌的MIC值分别为18.3 ± 0.6、23.1 ± 0.4和26.1 ± 0.5 µg/mL。
• Vilsmeier Reagent: An Efficient Reagent for the Transformation of 2-Aminobenzamides into Quinazolin-4(3<i>H</i>)-one Derivatives
  作者：Soghra Farzipour、Mina Saeedi、Mohammad Mahdavi、Hossein Yavari、Mohammadreza Mirzahekmati、Nasser Ghaemi、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1080/00397911.2013.811528

  日期：2014.2.16

  Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• JOSHI, VIDYA;CHAUDHARI, R. P.;MOGERA, S. R., INDIAN J. CHEM. B, 28,(1989) N, C. 431-434
  作者：JOSHI, VIDYA、CHAUDHARI, R. P.、MOGERA, S. R.

  DOI：——

  日期：——
• Joshi; Chaudhari; Mogera, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 5, p. 431 - 434
  作者：Joshi、Chaudhari、Mogera

  DOI：——

  日期：——