N-(4-ethoxyphenyl)benzo[d]oxazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-(4-ethoxyphenyl)benzo[d]oxazol-2-amine
• 英文别名: N-(4-ethoxyphenyl)-1,3-benzoxazol-2-amine
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: KDEXWPMJJXBHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基苯酚 在 氯化亚砜 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(4-ethoxyphenyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking study of N -arylbenzo[ d ]oxazol-2-amines as potential α-glucosidase inhibitors

  摘要：

  A novel series of N-arylbenzo[d]oxazol-2-amines (4a-4m) were synthesized and evaluated for their alpha-glucosidase inhibitory activity. Compounds 4f-4i, 4k and 4m displayed potent inhibitory activity against alpha-glucosidase with IC50 values in the range of 32.49 +/- 0.17-120.24 +/- 0.51 mu M as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of ot-glucosidase with an IC50 value of 32.49 +/- 0.17 mu M. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of alpha-glucosidase with a K-i value of 31.33 mu M. Binding interaction of compound 4g with alpha-glucosidase was explored by molecular docking simulation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.061

文献信息

• Cerniani; Passerini, Annali di Chimica, 1954, vol. 44, p. 3,4, 9
  作者：Cerniani、Passerini

  DOI：——

  日期：——
• Synthesis of N-Aryl-2-aminobenzoxazoles from Substituted Benzoxazole-2-thiol and 2-Chloro-N-arylacetamides in KOH-DMF System
  作者：Guang-cheng Wang、Jing Wang、Lu-yao Li、Shan Chen、Ya-ping Peng、Zhen-zhen Xie、Ming Chen、Bing Deng、Wen-biao Li

  DOI：10.3987/com-17-13712

  日期：——

  A simple and novel method for the synthesis of N-aryl-2-aminobenzoxazoles from substituted benzoxazole-2-thiol and 2-chloro-N-arylacetamides in KOH-DMF system has been developed. The present protocol provides an attractive approach to access various N-aryl-2-aminobenzoxazoles in moderate to good yields without using transition metal catalyst under very mild reaction condition.
• Synthesis, biological evaluation and molecular docking study of N -arylbenzo[ d ]oxazol-2-amines as potential α-glucosidase inhibitors
  作者：Guangcheng Wang、Zhiyun Peng、Jing Wang、Juan Li、Xin Li

  DOI：10.1016/j.bmc.2016.08.061

  日期：2016.11

  A novel series of N-arylbenzo[d]oxazol-2-amines (4a-4m) were synthesized and evaluated for their alpha-glucosidase inhibitory activity. Compounds 4f-4i, 4k and 4m displayed potent inhibitory activity against alpha-glucosidase with IC50 values in the range of 32.49 +/- 0.17-120.24 +/- 0.51 mu M as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of ot-glucosidase with an IC50 value of 32.49 +/- 0.17 mu M. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of alpha-glucosidase with a K-i value of 31.33 mu M. Binding interaction of compound 4g with alpha-glucosidase was explored by molecular docking simulation. (C) 2016 Elsevier Ltd. All rights reserved.