6-Bromo-2-(4-methoxyphenyl)-3,1-benzoxazin-4-one | 375832-95-4

• 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: 6-Bromo-2-(4-methoxyphenyl)-3,1-benzoxazin-4-one
• CAS: 375832-95-4
• 化学式: C₁₅H₁₀BrNO₃
• mdl: MFCD01186018
• 分子量: 332.153
• InChiKey: NVSIRVIUZMDBCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：

  6-Bromo-2-(4-methoxyphenyl)-3,1-benzoxazin-4-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 以42 %的产率得到6-bromo-3-amino-2-(4-methoxyphenyl)-quinazolin-4(3H)-one
  参考文献：
  名称：

  10.13005/ojc/400207

  摘要：

  The quinoline family comprises an appealing group of heterocyclic compounds, with quinazolinones and their synthetic analogs being of particular interest. To synthesize 3- amino 2-phenyl quinazolinones, anthranilic acid and its substituted derivatives were employed as initial materials. The MES method was utilized to evaluate the anticonvulsant activity of the developed substances on albino mice, with phenytoin serving as a benchmark anticonvulsant medication.The synthesized compounds demonstrated noteworthy anticonvulsant activity, comparable to that of established prescription medications. Among these compounds, Compound A-1 exhibited the highest level of activity. This indicates the potential of these synthetic analogs as effective anticonvulsants, with Compound A-1 standing out as particularly promising in this regard.Preliminary results indicate that certain quinazolinone derivatives exhibited promising anticonvulsant effects in the MES test. Further investigation into the mechanism of action and safety profile of these compounds is underway. The structure-activity relationships deduced from this study may guide the design of future anticonvulsant agents based on the quinazolinone scaffold.This research contributes to the ongoing efforts to discover new therapeutic options for epilepsy and provides valuable insights into the potential of quinazolinone derivatives as anticonvulsant agents. The findings underscore the importance of exploring diverse chemical structures in the quest for improved treatments for neurological disorders.

  DOI：

  10.13005/ojc/400207
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 2-氨基-5-溴苯甲酸 在 吡啶 作用下， 生成 6-Bromo-2-(4-methoxyphenyl)-3,1-benzoxazin-4-one
  参考文献：
  名称：

  Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.06.019

文献信息

• 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.
• 10.13005/ojc/400207
  作者：Yaduwanshi, Phool Singh、Singh, Sheelu、Sahapuriya, Prinsi、Dubey, Priyanka、Thakur, Jyoti、Yadav, Savita

  DOI：10.13005/ojc/400207

  日期：——

  The quinoline family comprises an appealing group of heterocyclic compounds, with quinazolinones and their synthetic analogs being of particular interest. To synthesize 3- amino 2-phenyl quinazolinones, anthranilic acid and its substituted derivatives were employed as initial materials. The MES method was utilized to evaluate the anticonvulsant activity of the developed substances on albino mice, with phenytoin serving as a benchmark anticonvulsant medication.The synthesized compounds demonstrated noteworthy anticonvulsant activity, comparable to that of established prescription medications. Among these compounds, Compound A-1 exhibited the highest level of activity. This indicates the potential of these synthetic analogs as effective anticonvulsants, with Compound A-1 standing out as particularly promising in this regard.Preliminary results indicate that certain quinazolinone derivatives exhibited promising anticonvulsant effects in the MES test. Further investigation into the mechanism of action and safety profile of these compounds is underway. The structure-activity relationships deduced from this study may guide the design of future anticonvulsant agents based on the quinazolinone scaffold.This research contributes to the ongoing efforts to discover new therapeutic options for epilepsy and provides valuable insights into the potential of quinazolinone derivatives as anticonvulsant agents. The findings underscore the importance of exploring diverse chemical structures in the quest for improved treatments for neurological disorders.