N-Hydroxy-5-methylfuran-2-carbimidoyl Chloride | 157991-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-Hydroxy-5-methylfuran-2-carbimidoyl Chloride
• 英文别名: N-hydroxy-5-methylfuran-2-carboximidoyl chloride
• CAS: 157991-79-2
• 化学式: C₆H₆ClNO₂
• 分子量: 159.572
• InChiKey: SGVGVIMWLQLYBG-UHFFFAOYSA-N

物化性质

• 沸点：
  273.6±42.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Hydroxy-5-methylfuran-2-carbimidoyl Chloride 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 5-hydroxy-5-methyl-3-(5-methylfuran-2-yl)-4-phenyl-2-isoxazoline
  参考文献：
  名称：

  Synthesis, Pharmacological Characterization, and Docking Analysis of a Novel Family of Diarylisoxazoles as Highly Selective Cyclooxygenase-1 (COX-1) Inhibitors

  摘要：

  3-(5-Chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6), a known selective cyclooxygenase-1 (COX-1) inhibitor, was used to design a new series of 3,4-diarylisoxazoles in order to improve its biochemical COX-1 selectivity and antiplatelet efficacy. Structure activity relationships were studied using human whole blood assays for COX-1 and COX-2 inhibition in vitro, and results showed that the simultaneous presence of S-methyl (or -CF3), 4-phenyl, and 5-chloro(-bromo or -methyl)furan-2-yl groups on the isoxazole core was essential for their selectivity toward COX-1. 3g, 3s, 3d were potent and selective COX-1 inhibitors that affected platelet aggregation in vitro through the inhibition of COX-1-dependent thromboxane (TX) A(2). Moreover, we characterized their kinetics of COX-1 inhibition. 3g, 3s, and 3d were more potent inhibitors of platelet COX-1 and aggregation than P6 (named 6) for their tighter binding to the enzyme. The pharmacological results were supported by docking simulations. The oral administration of 3d to mice translated into preferential inhibition of platelet-derived TXA(2) over protective vascular-derived prostac-yclin (PGI(2)).

  DOI：

  10.1021/jm301905a