(6-methyl-2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester | 787-65-5

• 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-methyl-2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester
• 英文别名: 6-Methyl-2-oxo-3-ethoxycarbonylmethylen-3,4-dihydro-2H-1,4-benzoxazin；Ethyl 2-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)acetate；ethyl 2-(6-methyl-2-oxo-4H-1,4-benzoxazin-3-ylidene)acetate
• CAS: 787-65-5
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: JXSJSUDHDQEVBH-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-2-硝基乙烯 、 (6-methyl-2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester 在 Fe₃O₄ on reduced graphene oxide nanocomposite 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以86%的产率得到ethyl 2-(4-chlorophenyl)-8-methyl-4-oxo-4H-benzo[b]pyrrolo[1,2-d]-[1,4]oxazine-3-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant

  摘要：

  Reduction of mitochondrial oxidative stress-mediated diseases is an important pharmaceutical objective in recent biomedical research. In this context, a series of novel pyrrolobenzoxazines (PyBs) framework with enormous diversity (compounds 5a-w) was synthesized by employing a low-temperature greener pathway, and antioxidant property of the synthesized compounds was successfully demonstrated on preclinical model goat heart mitochondria, in vitro. Copper ascorbate (Cu-As) was utilized as an oxidative stress generator. Out of screened PyBs, the compound possessing -OH and -OMe groups on benzene nucleus along with pyrrolobenzoxazine core moiety (compound 5w) displayed magnificent antioxidant property with a minimum effective dose of 66 mu M during the biochemical assessment. The ameliorative effect of synthesized pyrrolobenzoxazine moiety on levels of biomarkers of oxidative stress, antioxidant enzyme, activities of Krebs cycle and respiratory chain enzymes, mitochondrial morphology, and Ca2+ permeability of mitochondrial membrane was investigated in the presence of Cu-As. Furthermore, the binding mode of Cu-As by compound 5w was explored successfully using isothermal titration calorimetry (ITC) analysis.

  DOI：

  10.1021/acs.jmedchem.9b00717
• 作为产物：
  描述：

  邻氨基对甲苯酚 、 丁炔二酸二乙酯 以 乙醇 为溶剂， 生成 (6-methyl-2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester
  参考文献：
  名称：

  Die Reaktion von Acetylencarbonsäure mit Aminen. XIII. Substituierte 2-Oxo-3-äthoxycarbonylmethylen-3,4-dihydro-2H-1,4-benzoxazine

  摘要：

  DOI：

  10.1246/bcsj.37.1745

文献信息

• Die Reaktion von Acetylencarbonsäure mit Aminen. XIII. Substituierte 2-Oxo-3-äthoxycarbonylmethylen-3,4-dihydro-2H-1,4-benzoxazine
  作者：Yasuo Iwanami、Seiko Isoyama、Yoshihisa Kenjo

  DOI：10.1246/bcsj.37.1745

  日期：1964.12
• Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant
  作者：Tania Kundu、Bharati Bhattacharjee、Subhenjit Hazra、Arnab K. Ghosh、Debasish Bandyopadhyay、Animesh Pramanik

  DOI：10.1021/acs.jmedchem.9b00717

  日期：2019.7.11

  Reduction of mitochondrial oxidative stress-mediated diseases is an important pharmaceutical objective in recent biomedical research. In this context, a series of novel pyrrolobenzoxazines (PyBs) framework with enormous diversity (compounds 5a-w) was synthesized by employing a low-temperature greener pathway, and antioxidant property of the synthesized compounds was successfully demonstrated on preclinical model goat heart mitochondria, in vitro. Copper ascorbate (Cu-As) was utilized as an oxidative stress generator. Out of screened PyBs, the compound possessing -OH and -OMe groups on benzene nucleus along with pyrrolobenzoxazine core moiety (compound 5w) displayed magnificent antioxidant property with a minimum effective dose of 66 mu M during the biochemical assessment. The ameliorative effect of synthesized pyrrolobenzoxazine moiety on levels of biomarkers of oxidative stress, antioxidant enzyme, activities of Krebs cycle and respiratory chain enzymes, mitochondrial morphology, and Ca2+ permeability of mitochondrial membrane was investigated in the presence of Cu-As. Furthermore, the binding mode of Cu-As by compound 5w was explored successfully using isothermal titration calorimetry (ITC) analysis.