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

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-phenoxyphenyl)benzo[d]oxazol-2-amine
• 英文别名: N-(4-phenoxyphenyl)-1,3-benzoxazol-2-amine
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: DZPMYRHMEVVHJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-(4-phenoxyphenyl)guanidine carbonate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.0h， 生成 N-(4-phenoxyphenyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  通过胍环二亚胺活化在胍碳中心进行亲核取代

  摘要：

  尽管胍碳中心具有缺电子性质，但由于胍基团的共振稳定性，这些位点的亲核反应尚未发展。我们提出了一种胍 C-N 键取代策略，该策略需要形成胍环二亚胺 (GCDI) 结构，从而有效地破坏胍基团的共振结构。在酸添加剂的存在下，GCDIs 的胍碳中心与各种胺和醇发生亲核取代反应。

  DOI：

  10.1021/acs.orglett.1c03473

文献信息

• 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.