4-benzyl-7-(morpholinomethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one | 1580053-32-2

• 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: 4-benzyl-7-(morpholinomethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 4-Benzyl-7-(morpholin-4-ylmethyl)-1,4-benzoxazin-3-one；4-benzyl-7-(morpholin-4-ylmethyl)-1,4-benzoxazin-3-one
• CAS: 1580053-32-2
• 化学式: C₂₀H₂₂N₂O₃
• 分子量: 338.406
• InChiKey: FHLGIJIZUYHIPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-溴-4-羟基苯甲醇 在 三溴化磷 、 potassium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-benzyl-7-(morpholinomethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  The synthesis of 4,7-disubstituted-2H-benzo[b][1,4]-oxazin-3(4H)-ones using Smiles rearrangement and their in vitro evaluation as platelet aggregation inhibitors

  摘要：

  A series of novel benzo[b][1,4] oxazin-3(4H)-one derivatives were synthesized as platelet aggregation inhibitors for structure-activity relationships (SAR) analysis. The synthetic pattern, involved Smiles rearrangement for the preparation of benzoxazine, was proven to be more efficient than the conventional methods. Biological evaluation demonstrated that among all the synthesized compounds, compound 9u (IC50 = 9.20 mu M) exhibited the most potent inhibition activity compared with aspirin, the positive control (IC50 = 7.07 mu M). Molecular docking revealed that these set of compounds could be the GPIIb/IIIa antagonist for that they could be situated in the binding site of GPIIb/IIIa receptor quite well. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.014

文献信息

• The synthesis of 4,7-disubstituted-2H-benzo[b][1,4]-oxazin-3(4H)-ones using Smiles rearrangement and their in vitro evaluation as platelet aggregation inhibitors
  作者：Shuai Xia、Ji-Qiang Liu、Xiu-Hua Wang、Ye Tian、Yu Wang、Jing-Huan Wang、Liang Fang、Hua Zuo

  DOI：10.1016/j.bmcl.2014.02.014

  日期：2014.3

  A series of novel benzo[b][1,4] oxazin-3(4H)-one derivatives were synthesized as platelet aggregation inhibitors for structure-activity relationships (SAR) analysis. The synthetic pattern, involved Smiles rearrangement for the preparation of benzoxazine, was proven to be more efficient than the conventional methods. Biological evaluation demonstrated that among all the synthesized compounds, compound 9u (IC50 = 9.20 mu M) exhibited the most potent inhibition activity compared with aspirin, the positive control (IC50 = 7.07 mu M). Molecular docking revealed that these set of compounds could be the GPIIb/IIIa antagonist for that they could be situated in the binding site of GPIIb/IIIa receptor quite well. (C) 2014 Elsevier Ltd. All rights reserved.