3-氨基-2-(4-氯苯基)喹唑啉-4-酮 | 63002-70-0

• 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-氨基-2-(4-氯苯基)喹唑啉-4-酮
• 英文名称: 3-amino-2-(4-chlorophenyl)quinazolin-4(3H)-one
• 英文别名: 3-amino-2-(4-chlorophenyl)quinazolin-4-one
• CAS: 63002-70-0
• 化学式: C₁₄H₁₀ClN₃O
• 分子量: 271.706
• InChiKey: IFVAHOZNQQBOLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基-2-(4-氯苯基)喹唑啉-4-酮 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以70%的产率得到2-(4-chlorophenyl)-4(3H)-quinazolinone
  参考文献：
  名称：

  Vaid, Radhe K.; Rao, B. Venkateswara; Kaushik, Beena, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 376 - 377

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 在 一水合肼 作用下， 以 吡啶 、 xylene 为溶剂， 反应 2.08h， 生成 3-氨基-2-(4-氯苯基)喹唑啉-4-酮
  参考文献：
  名称：

  Reddy, Ch. K.; Reddy, P. S. N.; Ratnam, C. V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 902 - 904

  摘要：

  DOI：

文献信息

• Synthesis of 3-Aminoquinazolinones via a SnCl₂-Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles
  作者：Mohamed Elagawany、Lingaiah Maram、Bahaa Elgendy

  DOI：10.1021/acs.joc.3c01973

  日期：2023.12.15

  Herein, we developed a new SnCl2-mediated ANRORC (addition of nucleophile, ring-opening, and ring-closure)-like rearrangement for the synthesis of 3-amino-2-substituted-quinazolin-4(3H)-one from 2-(2-nitrophenyl)-5-substituted-1,3,4-oxadiazole. The new method is solvent-dependent and features the use of a green solvent system (i.e., ethanol/water), high yields, and simple workup. The reduced product

  在此，我们开发了一种新的SnCl 2介导的ANRORC（亲核试剂加成、开环和闭环）类重排，用于合成3-氨基-2-取代-喹唑啉-4(3 H )-one 2-(2-硝基苯基)-5-取代-1,3,4-恶二唑。新方法依赖于溶剂，具有使用绿色溶剂系统（即乙醇/水）、高产率和简单后处理的特点。将溶剂改为乙腈即可独家合成还原产物。
• Quinazolinone-Schiff's Base hybrids as Phosphodiesterase 4B inhibitors with dual activity against COPD and Lung Cancer
  作者：Mostafa Mansour、Mohammed El-Saadi、Noha Amin、Joshua Canzoneri、Adam Keeton、Gary Piazza、hamdy abdelrahman

  DOI：10.21608/ejchem.2020.28992.2624

  日期：2020.6.6
• Rao, Gopal Krishna; Rajasekaran; Sanjay Pai, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 293 - 294
  作者：Rao, Gopal Krishna、Rajasekaran、Sanjay Pai

  DOI：——

  日期：——
• Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
  作者：Mahmud Tareq Hassan Khan、Rasool Khan、Yimingjiang Wuxiuer、Mohammad Arfan、Manzoor Ahmed、Ingebrigt Sylte

  DOI：10.1016/j.bmc.2010.04.083

  日期：2010.6.15

  A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 mu M (compound 3) to 122,637 mu M (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 mu M) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 mu M) were found to be the most potent inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and antitubercular activity of novel pyrazole–quinazolinone hybrid analogs
  作者：Unnat Pandit、Amit Dodiya

  DOI：10.1007/s00044-012-0351-0

  日期：2013.7

  A series of 2-(substituted-phenyl)-3-(((3-(pyridin-4-yl)-1-(p-tolyl)-1H-pyrazol-4-yl)methylene)amino)-quinazolin-4(3H)-ones have been synthesized. The structures of the synthesized compounds were assigned on the basis of IR, H-1 NMR, C-13 NMR, and mass spectral data, while their abilities to inhibit growth of Mycobacterium tuberculosis in vitro have been determined. The results show that compounds 5a, 5c, 5d, 5g, and 5k exhibited excellent antitubercular activity with percentage inhibition of 96, 90, 94, 93, and 92, respectively at a minimum inhibitory concentration (MIC) of < 6.25 mu g/mL, whereas compounds 5b, 5e, 5f, 5h, 5i, 5j, and 5l exhibited moderate- to- good antitubercular activity with percentage inhibition of 68, 70, 67, 64, 59, 73, and 67, respectively, at a MIC of > 6.25 mu g/mL. From the secondary screening, the actual MIC of compounds 5a, 5c, 5d, 5g, and 5k are < 3.125.