7-chloro-2-(4-methoxyphenyl)-4-H-benzo[d][1,3]oxazin-4-one | 500872-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-chloro-2-(4-methoxyphenyl)-4-H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-Chloro-2-(4-methoxyphenyl)-3,1-benzoxazin-4-one
• CAS: 500872-79-7
• 化学式: C₁₅H₁₀ClNO₃
• 分子量: 287.702
• InChiKey: VREMNZKPJMUMDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-2-(4-methoxyphenyl)-4-H-benzo[d][1,3]oxazin-4-one 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  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.

  DOI：

  10.3109/14756366.2013.845820
• 作为产物：
  描述：

  在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 7-chloro-2-(4-methoxyphenyl)-4-H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  PhI(OAc) 2介导的邻氨基苯甲酸和芳香醛一锅法合成苯并恶嗪酮

  摘要：

  一种合成 2-芳基-4H-苯并[d][1,3]恶嗪-4-酮的新方法已通过席夫碱与（二乙酰氧基碘）苯的环化而开发。这种从邻氨基苯甲酸和芳香醛开始的新方案的显着特点是反应时间短、反应条件温和、产率高。

  DOI：

  10.3184/174751912x13285455672357

文献信息

• Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4<i>H</i>-Benzo[<i>d</i>][1,3]oxazin-4-ones and 4-Benzylidene-2-aryloxazol-5(4<i>H</i>)-ones
  作者：Long Wang、Yi-Bi Xie、Nian-Yu Huang、Jia-Ying Yan、Wei-Min Hu、Ming-Guo Liu、Ming-Wu Ding

  DOI：10.1021/acscatal.6b00165

  日期：2016.6.3

  copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step

  与醛，酮，酰胺和酯的aza-Wittig反应相比，酸酐的aza-Wittig反应总是被忽略，这应该是Wittig反应的重要组成部分。在这里，酸酐的aza-Wittig反应和酸酐的aza-Wittig催化反应均以高收率开发，这为合成4 H-苯并[ d ] [1,3]恶嗪-4-酮和4-亚苄基-2-芳基恶唑-5（4 H）-那些。使用了铜催化的氧化膦还原的策略，发现该策略对这种转化有效。另外，实现了羧酸的一锅催化的氮杂-维蒂希反应。此外，NMR实验和Hammett曲线记录了酸酐的催化氮杂-维蒂希反应过程，这直接证明了铜催化的废氧化膦的还原是该转化过程中的关键步骤。
• Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents
  作者：E. Manivannan、S.C. Chaturvedi

  DOI：10.1016/j.bmc.2011.06.019

  日期：2011.8

  In our effort to identify potent gastric sparing anti-inflammatory agents, a series of methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl quinazolinones were designed by analogue-based design strategy and synthesized for biological evaluation. Subsequently, the compounds were evaluated for both cyclooxygenase inhibitions by ovine COX assay and carrageenan-induced rat paw edema assay. All the methyl sulfonyl substituted quinazolinones were exhibited promising anti-inflammatory activity. In particular, 6-bromo-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one (18), 7-chloro-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one (19), 3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-3H-quinazolin-4-one (21) and 6-bromo-3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-3H-quinazolin-4-one (22) emerged as the most active compounds in the series. The results of ulcerogenic activity assay suggest that these compounds are gastric safe compared to indomethacin. The molecular docking analysis was performed to understand the binding interactions of these compounds to COX-2 enzyme. The results from the present investigation suggests that 2,3-diaryl quinazolinones as a promising template for the design of new gastric safe anti-inflammatory agents, which can be further explored for potential anti-inflammatory activity. (C) 2011 Elsevier Ltd. All rights reserved.
• 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
• 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.
• PhI(OAc)₂-Mediated One-Pot Synthesis of Benzoxazinones from Anthranilic Acids and Aromatic Aldehydes
  作者：Yuanyuan Xie、Suping Wang

  DOI：10.3184/174751912x13285455672357

  日期：2012.3

  way to synthesise 2-aryl-4H-benzo[d][1,3]oxazin-4-ones has been developed by the cyclisation of Schiff bases with (diacetoxyiodo)benzene. The salient features of this new protocol which starts from an anthranilic acid and an aromatic aldehyde, are short reaction time, mild reaction conditions and good yields.

  一种合成 2-芳基-4H-苯并[d][1,3]恶嗪-4-酮的新方法已通过席夫碱与（二乙酰氧基碘）苯的环化而开发。这种从邻氨基苯甲酸和芳香醛开始的新方案的显着特点是反应时间短、反应条件温和、产率高。