N-(2,4-dichlorophenyl)benzo[d]oxazol-2-amine | 39190-19-7

• 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-(2,4-dichlorophenyl)benzo[d]oxazol-2-amine
• 英文别名: N-(2,4-dichlorophenyl)-1,3-benzoxazol-2-amine
• CAS: 39190-19-7
• 化学式: C₁₃H₈Cl₂N₂O
• 分子量: 279.125
• InChiKey: SLIOXWJNBCJZDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.06
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-巯基苯并恶唑 在 氯化亚砜 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(2,4-dichlorophenyl)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

• Substituted 2-anilinobenzoxazoles used as immunosuppressive agents
  申请人：Eli Lilly and Company

  公开号：US04088770A1

  公开（公告）日：1978-05-09

  Compositions comprising certain 2-(substituted anilino)benzoxazoles, such as 2-[4-bromo-3-(trifluoromethyl)anilino]benzoxazole, and methods for using same as immunosuppressive agents, antifertility agents, for the prophylaxis of Marek's disease in chickens and as herbicides.

  包含某些2-(取代苯胺基)苯并噁唑类化合物的组合物，例如2-[4-溴-3-(三氟甲基)苯胺基]苯并噁唑，以及使用它们作为免疫抑制剂、抗生育剂、用于预防鸡的马立克病，以及作为除草剂的方法。
• Substituted 2-anilinobenzoxazoles
  申请人：Eli Lilly and Company

  公开号：US04275210A1

  公开（公告）日：1981-06-23

  Compositions comprising certain 2-(substituted anilino)benzoxazoles, such as 2-[4-bromo-3-(trifluoromethyl)-anilino]benzoxazole, and methods for using same as immunosuppressive agents, antifertility agents, for the prophylaxis of Marek's disease in chickens and as herbicides.

  包括某些2-(取代苯胺基)苯并噁唑的组合物，例如2-[4-溴-3-(三氟甲基)-苯胺基]苯并噁唑，以及将其用作免疫抑制剂、抗生育剂、用于预防鸡马立克病和除草剂的方法。
• 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.
• US4088770A
  申请人：——

  公开号：US4088770A

  公开（公告）日：1978-05-09
• US4275210A
  申请人：——

  公开号：US4275210A

  公开（公告）日：1981-06-23