5-Butoxymethyl-3-(3-cyano-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid | 1026430-47-6

• 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: 5-Butoxymethyl-3-(3-cyano-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid
• 英文别名: 5-(butoxymethyl)-3-(3-cyanophenyl)-4H-1,2-oxazole-5-carboxylic acid
• CAS: 1026430-47-6
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: UVIYEKIUKIDBBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Butoxymethyl-3-(3-cyano-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid 在 盐酸 、 氯化亚砜 、 ammonium acetate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 1.0h， 生成 5-isoxazolecarboxamide, 3-<3-(aminoiminomethyl)phenyl>-N-<<5-<2'-(aminosulfonyl)<1,1'-biphenyl>-4-yl>-4,5-dihydro-5-(n-butoxymethyl)->>
  参考文献：
  名称：

  Design and Synthesis of Isoxazoline Derivatives as Factor Xa Inhibitors. 2

  摘要：

  Intravascular clot formation is an important factor in a number of cardiovascular diseases, Therefore, the prevention of blood coagulation has become a major target for new therapeutic agents. One attractive approach is the inhibition of factor Xa (FXa), the enzyme directly responsible for thrombin activation. Herein we report a series of isoxazoline derivatives which are potent FXa inhibitors. Optimization of the side chain at the quaternary position of the isoxazoline ring led to SK549 which showed subnanomolar FXa potency (K-i 0.52 nM). SK549 shows good selectivity for FXa compared to thrombin and trypsin, potent antithrombotic effect in the rabbit arterio-venous thrombosis model, and improved pharmacokinetics relative to other compounds evaluated from this series.

  DOI：

  10.1021/jm980406a
• 作为产物：
  描述：

  Methyl 2-(butoxymethyl)prop-2-enoate 在 lithium hydroxide 、 sodium hypochlorite 作用下， 以 四氢呋喃 为溶剂， 生成 5-Butoxymethyl-3-(3-cyano-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of Isoxazoline Derivatives as Factor Xa Inhibitors. 2

  摘要：

  Intravascular clot formation is an important factor in a number of cardiovascular diseases, Therefore, the prevention of blood coagulation has become a major target for new therapeutic agents. One attractive approach is the inhibition of factor Xa (FXa), the enzyme directly responsible for thrombin activation. Herein we report a series of isoxazoline derivatives which are potent FXa inhibitors. Optimization of the side chain at the quaternary position of the isoxazoline ring led to SK549 which showed subnanomolar FXa potency (K-i 0.52 nM). SK549 shows good selectivity for FXa compared to thrombin and trypsin, potent antithrombotic effect in the rabbit arterio-venous thrombosis model, and improved pharmacokinetics relative to other compounds evaluated from this series.

  DOI：

  10.1021/jm980406a

文献信息

• HERBIZID WIRKSAME 3-PHENYLISOXAZOLINDERIVATE
  申请人：Bayer CropScience AG

  公开号：EP2900645B1

  公开（公告）日：2019-08-21