7-((phenylamino)methyl)-4-propyl-2H-benzo[b][1,4]oxazin-3(4H)-one | 1354789-47-1

• 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: 7-((phenylamino)methyl)-4-propyl-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 7-(Anilinomethyl)-4-propyl-1,4-benzoxazin-3-one
• CAS: 1354789-47-1
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: NUXZQROZPSRWSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Bromo-4-(phenyliminomethyl)phenol 在 sodium tetrahydroborate 、 potassium carbonate 、 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 7-((phenylamino)methyl)-4-propyl-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  Synthesis of 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives as platelet aggregation inhibitors

  摘要：

  Novel 2H-benzo[b][1,4] oxazin-3(4H)-ones have been synthesized by condensation, reduction, O-alkylation and Smiles rearrangement using 3-bromo-4-hydroxy benzaldehyde, anilines, and chloroacetyl chloride as starting materials. All the synthesized compounds have been characterized by (1)H NMR, (13)C NMR, and HRMS, and tested for the inhibitory ability on platelet aggregation. The results have shown that the ADP (adenosine 5'-diphosphate)-induced platelet aggregation was inhibited by 7a-g with the IC(50) value at 10.14-18.83 lmol/L. Compound 7a exhibited the most potent inhibitory effect (IC(50) = 10.14 mu mol/L) among all the compounds, but less potent than the control drug ticlopidine (3.18 mu mol/L) and aspirin (6.07 mu mol/L). The preliminary structure-activity relationship (SAR) was initially investigated in the study. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.027

文献信息

• Synthesis of 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives as platelet aggregation inhibitors
  作者：Xiao Tian、Li-Ying Wang、Shuai Xia、Zhu-Bo Li、Xing-Hui Liu、Yuan Yuan、Liang Fang、Hua Zuo

  DOI：10.1016/j.bmcl.2011.11.027

  日期：2012.1

  Novel 2H-benzo[b][1,4] oxazin-3(4H)-ones have been synthesized by condensation, reduction, O-alkylation and Smiles rearrangement using 3-bromo-4-hydroxy benzaldehyde, anilines, and chloroacetyl chloride as starting materials. All the synthesized compounds have been characterized by (1)H NMR, (13)C NMR, and HRMS, and tested for the inhibitory ability on platelet aggregation. The results have shown that the ADP (adenosine 5'-diphosphate)-induced platelet aggregation was inhibited by 7a-g with the IC(50) value at 10.14-18.83 lmol/L. Compound 7a exhibited the most potent inhibitory effect (IC(50) = 10.14 mu mol/L) among all the compounds, but less potent than the control drug ticlopidine (3.18 mu mol/L) and aspirin (6.07 mu mol/L). The preliminary structure-activity relationship (SAR) was initially investigated in the study. (C) 2011 Elsevier Ltd. All rights reserved.