3-(5-methylthiophen-2-yl)-1,2-oxazol-5-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-(5-methylthiophen-2-yl)-1,2-oxazol-5-amine
• 化学式: C₈H₈N₂OS
• 分子量: 180.23
• InChiKey: GYANVOWXBCWRGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-methylthiophen-2-yl)-1,2-oxazol-5-amine 在 吡啶 、 氯磺酸 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 N-[3-(5-methyl-4-sulfamoylthiophen-2-yl)-1,2-oxazol-5-yl]acetamide
  参考文献：
  名称：

  Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

  摘要：

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.018
• 作为产物：
  描述：

  3-oxo-3-(5-methylthiophene-2-yl)propanenitrile 在 羟胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 14.0h， 以71%的产率得到3-(5-methylthiophen-2-yl)-1,2-oxazol-5-amine
  参考文献：
  名称：

  Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

  摘要：

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.018