methyl 2-(4-chlorophenyl)-4-oxo-4H-benzo[b]pyrrolo[1,2-d]-[1,4]oxazine-3-carboxylate | 1536473-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 2-(4-chlorophenyl)-4-oxo-4H-benzo[b]pyrrolo[1,2-d]-[1,4]oxazine-3-carboxylate
• 英文别名: Methyl 2-(4-chlorophenyl)-4-oxopyrrolo[2,1-c][1,4]benzoxazine-3-carboxylate
• CAS: 1536473-38-7
• 化学式: C₁₉H₁₂ClNO₄
• 分子量: 353.762
• InChiKey: ULFCHYUGXVATIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  丁炔二酸二甲酯 在 Fe₃O₄ on reduced graphene oxide nanocomposite 作用下， 以 neat (no solvent) 为溶剂， 反应 1.17h， 生成 methyl 2-(4-chlorophenyl)-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

文献信息

• Trifluoroacetic acid-promoted Michael addition–cyclization reactions of vinylogous carbamates
  作者：Ram Tilak Naganaboina、Amrita Nayak、Rama Krishna Peddinti

  DOI：10.1039/c4ob00437j

  日期：——

  A simple and efficient methodology has been developed for the synthesis of pyrrolobenzoxazine and 3-arylamino coumarin derivatives promoted by trifluoroacetic acid. The initial step in the current protocol involves a Michael addition of the 1,4-benzoxazinone derivatives to the Michael acceptors and subsequent cyclization.

  已开发出一种简单高效的方法，通过三氟乙酸促进合成吡咯苯并噁嗪和3-芳基氨基香豆素衍生物。当前方案的初始步骤涉及1,4-苯并噁嗪衍生物与Michael受体的Michael加成，然后进行环化反应。
• 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.