3-氨基-2-(4-硝基苯基)喹唑啉-4-酮 | 63002-71-1

• 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-硝基苯基)喹唑啉-4-酮
• 英文名称: 3-amino-2-(4-nitrophenyl)quinazolin-4(3H)-one
• 英文别名: 3-Amino-2-(4-nitrophenyl)quinazolin-4-one
• CAS: 63002-71-1
• 化学式: C₁₄H₁₀N₄O₃
• 分子量: 282.258
• InChiKey: SBIROOHZJZRBTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 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：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氨基-2-(4-硝基苯基)喹唑啉-4-酮 在 (1S,2S,4S,5R)-1-(2,4-bis(trifluoromethyl)benzyl)-2-((S)-(3-((1R,2S)-2-hydroxy-1,2-diphenylethyl)ureido)(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 21.25h， 生成
  参考文献：
  名称：

  相转移催化烷基化不对称合成 N-N 轴手性化合物

  摘要：

  N-N 轴向手性骨架是天然产物、药物和功能材料中的重要结构基序。在此，我们公开了一种通过相转移催化不对称合成 N-N 轴向手性化合物的方法。以高产率制备了多种 N-N 轴向手性喹唑啉酮衍生物，具有优异的立体选择性。此外，该协议的合成效用通过产物的大规模反应和转化得到证明。密度泛函理论计算提供了对该机制的深入了解。

  DOI：

  10.1021/acs.orglett.1c04028
• 作为产物：
  描述：

  2-(4-硝基苯基)-4H-3,1-苯并恶嗪-4-酮 在 一水合肼 作用下， 以 乙醚 为溶剂， 以85%的产率得到3-氨基-2-(4-硝基苯基)喹唑啉-4-酮
  参考文献：
  名称：

  一些具有生物学意义的新苯并恶嗪衍生物的合成

  摘要：

  通过 3amino-2-aryl-4-quinazolone 和芳香醛的缩合，已实现了许多生物学上重要的亚氨基-喹唑酮类化合物的合成。

  DOI：

  10.1515/hc.2003.9.5.499

文献信息

• Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents
  作者：Mujeeb Ur Rahman、Ankita Rathore、Anees A. Siddiqui、Gazala Parveen、M. Shahar Yar

  DOI：10.3109/14756366.2013.845820

  日期：2014.10.1

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.
• Synthesis and biological evaluation of certain 3-substituted benzylideneamino-2-(4-nitrophenyl)quinazolin-4(3<i>H</i>)-one derivatives
  作者：Ahmed M. Alafeefy、Amani S. Awaad、Hatem A. Abdel-Aziz、Reham M. El-Meligy、Mohamed E. Zain、Mounerah R. Al-Outhman、Abir B. Bacha

  DOI：10.3109/14756366.2014.915398

  日期：2015.3.4

  Certain new 3H-quinazolin-4-one Schiff's bases were synthesized and screened for their activities against ulcerative colitis "UC''. Their activity against phospholipase A2 and protease enzymes was also investigated. Some compounds possessed remarkable effect with different potentials against acetic acid-induced colitis model in rats. Compound 14 (50 mg/kg) was more effective than dexamesathone (0.01 mg/kg). It produced 79.78% protection of control colitis; however, compound 13 produced 75.80% protection and was considered as effective as dexamesathone with 75.30% protection. The observed results could be explained partially by their anti-inflammatory activities which appear as phospholipase A2 (hGIIA) and/or through protease inhibitor potentials. However, all the compounds under test showed preferential inhibition towards hG-IIA type of PLA2 rather than DrG-IB with varying degrees. Interestingly, compounds 14, 13, 12 and 11 displayed excellent inhibitory activity against phospholipase A2 accompanied by protease inhibitory profile.
• 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
• 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
  作者：Reddy, Ch. K.、Reddy, P. S. N.、Ratnam, C. V.

  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.