2-(5-methylfuran-2-yl)quinazolin-4(3H)-one | 128373-25-1

• 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-(5-methylfuran-2-yl)quinazolin-4(3H)-one
• 英文别名: 2-(5-Methylfuran-2-yl)-3,4-dihydroquinazolin-4-one；2-(5-methylfuran-2-yl)-3H-quinazolin-4-one
• CAS: 128373-25-1
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: UNZNFBNEWJIFGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-dihydro-2-(5-methylfuran-2-yl)-quinazolin-4(1H)-one 在 air 作用下， 以 氯仿 为溶剂， 反应 0.33h， 以40%的产率得到2-(5-methylfuran-2-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Light induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones

  摘要：

  Light induced oxidation of various of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones (DHQZs) results smoothly the formation of quinazolin-4(3H)-ones (QZs) product. The electronic nature of the substituent on the 2-position and also the nature of solvent affect the rate of reaction, which supports the proposed mechanism based on the electron-transfer induced photo-oxidation. Analysis of the computational results obtained at the DFT-B3LYP/6-31++G** level of theory supports the mechanism in which the first electron removal occurs preferably from the N1 atom of the heterocyclic ring. In contrast to the solution photochemistry, no changes have been observed by irradiation in the solid state. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.07.008

文献信息

• Electro-oxidative cyclization: access to quinazolinones <i>via</i> K₂S₂O₈ without transition metal catalyst and base
  作者：Yongzhi Hu、Huiqing Hou、Ling Yu、Sunying Zhou、Xianghua Wu、Weiming Sun、Fang Ke

  DOI：10.1039/d1ra05092c

  日期：——

  A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure

  AK 2 S 2 O 8促进了伯醇与2-氨基苯甲酰胺的氧化串联环化以合成喹唑啉酮，在没有过渡金属和碱的不分电解条件下成功实现。该协议的主要特点是利用 K 2 S 2 O 8作为一种廉价且易于处理的自由基替代物，可以通过简单的程序有效地促进反应，从而通过形成氮杂环在恒定电流下以一锅法在室温下直接氧化环化。由于使用了连续流动的电化学装置，这种绿色、温和、实用的电合成具有高效率和优异的官能团耐受性，并且易于放大。
• Electrochemical synthesis of quinazolinone <i>via</i> I₂-catalyzed tandem oxidation in aqueous solution
  作者：Huiqing Hou、Xinhua Ma、Yingying Lin、Jin Lin、Weiming Sun、Lei Wang、Xiuzhi Xu、Fang Ke

  DOI：10.1039/d1ra02706a

  日期：——

  green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C–H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then

  开发在水性介质中使用生物相容性催化剂合成喹唑啉酮的方案将有助于解决使用绿色和可持续化学合成它们的困难。在此，使用 I 2与电化学合成配合会引起 C-H 氧化反应，据报道，当使用水作为环境友好溶剂在室温下获得广泛的喹唑啉酮时。反应机理有力地表明，I 2协同电化学促进醇的氧化，然后有效地将酰胺环化为各种喹唑啉酮。
• Synthesis and structure–activity relationship study of novel quinazolinone-based inhibitors of MurA
  作者：Martina Hrast、Kaja Rožman、Marko Jukič、Delphine Patin、Stanislav Gobec、Matej Sova

  DOI：10.1016/j.bmcl.2017.05.064

  日期：2017.8

  is essential for peptidoglycan biosynthesis, and is therefore an important target for antibacterial drug discovery. We report the synthesis, in silico studies and extensive structure–activity relationships of a series of quinazolinone-based inhibitors of MurA from Escherichia coli. 3-Benzyloxyphenylquinazolinones showed promising inhibitory potencies against MurA, in the low micromolar range, with an

  MurA是肽聚糖生物合成必不可少的细胞内细菌酶，因此是抗菌药物发现的重要靶标。我们报告了一系列来自大肠杆菌的MurA的基于喹唑啉酮的抑制剂的合成，计算机模拟研究和广泛的结构-活性关系。3-苯甲氧基苯基喹唑啉酮类化合物在低微摩尔范围内显示出对MurA的抑制作用，最有效的衍生物的IC 50为8 µM（58）。此外，呋喃基取代的喹唑啉酮（38，46）的抗菌活性令人振奋，MIC浓度从1 µg / mL到8 µg / mL，并具有其MurA抑制能力。这些数据代表了开发新型抗菌剂以对抗不断增加的细菌耐药性的重要一步。
• Syntheses based on furancarboxylic acid amides. 1. Synthesis and structure of 2-(5-R-2-furyl)-4-oxoquinazolines
  作者：I. N. Kozlovskaya、L. A. Badovskaya、V. E. Zavodnik、Z. I. Tyukhteneva

  DOI：10.1007/bf00481515

  日期：1989.11
• KOZLOVSKAYA, I. N.;BADOVSKAYA, L. A.;ZAVODNIK, V. E.;TYUXTENEVA, Z. I., XIMIYA GETEROTSIKL. SOED.,(1989) N1, S. 1463-1466
  作者：KOZLOVSKAYA, I. N.、BADOVSKAYA, L. A.、ZAVODNIK, V. E.、TYUXTENEVA, Z. I.

  DOI：——

  日期：——