ethyl 4-oxo-2-phenyl-4H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-3-carboxylate | 1536473-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4-oxo-2-phenyl-4H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-3-carboxylate
• 英文别名: Ethyl 4-oxo-2-phenylpyrrolo[2,1-c][1,4]benzoxazine-3-carboxylate
• CAS: 1536473-34-3
• 化学式: C₂₀H₁₅NO₄
• 分子量: 333.343
• InChiKey: OQRZNLKBONPARL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  丁炔二酸二乙酯 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 ethyl 4-oxo-2-phenyl-4H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-3-carboxylate
  参考文献：
  名称：

  合成吡咯并[2,1-c] [1,4]苯并恶嗪和吡咯并[1,2-a]喹喔啉的新方法。

  摘要：

  有效合成烷基4,5-二氢-4-氧代-2-苯基吡咯并[2,1-c] [1,4]苯并恶嗪-3-羧酸酯和烷基4,5-二氢-4-氧代-2-苯基吡咯并描述了[1,2-a]喹喔啉-3-羧酸盐。这涉及使用对甲苯磺酸作为催化剂的邻氨基苯酚或邻苯二胺，炔属酯和β-硝基苯乙烯衍生物之间的三组分反应。

  DOI：

  10.2174/1386207316666131227150430

文献信息

• One-pot synthesis of novel pyrrolo-1,4-benzoxazines via a three-component reaction of 2-amino phenols, acetylenic esters and nitrostyrene derivatives
  作者：Loghman Moradi、Mohammad Piltan、Hedieh Rostami

  DOI：10.1016/j.cclet.2013.10.009

  日期：2014.1

  A simple and efficient synthetic protocol has been developed using a one-pot, three-component reaction involving 2-amino phenols, dialkyl acetylene dicarboxylates and nitrostyrene derivatives. Utilizing this protocol, a variety of novel pyrrolo-1,4-benzoxazine derivatives were synthesized in excellent yields. (C) 2013 Loghman Moradi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• 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.