3-(3-Cyano-phenyl)-5-ethoxymethyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester | 1027205-06-6

• 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: 3-(3-Cyano-phenyl)-5-ethoxymethyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester
• 英文别名: methyl 3-(3-cyanophenyl)-5-(ethoxymethyl)-4H-1,2-oxazole-5-carboxylate
• CAS: 1027205-06-6
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: KMKUAJIRONLWNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-Cyano-phenyl)-5-ethoxymethyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3-Cyano-phenyl)-5-ethoxymethyl-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
• 作为产物：
  描述：

  2-(溴甲基)丙烯酸甲酯 在 sodium hypochlorite 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 Petroleum ether 为溶剂， 反应 12.0h， 生成 3-(3-Cyano-phenyl)-5-ethoxymethyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester
  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

• 3-PHENYLISOXAZOLIN DERIVATIVES WITH HERBICIDAL ACTION
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150245615A1

  公开（公告）日：2015-09-03

  3-Phenylisoxazoline derivatives of the formula (I), and the use thereof as herbicides, are described. In this formula (I), X 2 to X 6 and R 1 to R 3 are radicals such as hydrogen, halogen, and organic radicals such as substituted alkyl. W* is carboxyl, cyano or CHO.

  描述了公式（I）的3-苯基异噁唑啉衍生物及其作为除草剂的用途。 在这个公式（I）中，X2到X6和R1到R3是氢、卤素和有机基团（如取代烷基）等基团。W*是羧基、氰基或CHO。
• HERBIZID WIRKSAME 3-PHENYLISOXAZOLINDERIVATE
  申请人：Bayer CropScience AG

  公开号：EP2900645A1

  公开（公告）日：2015-08-05
• US9585392B2
  申请人：——

  公开号：US9585392B2

  公开（公告）日：2017-03-07
• Design and Synthesis of Isoxazoline Derivatives as Factor Xa Inhibitors. 2
  作者：Mimi L. Quan、Christopher D. Ellis、Ann Y. Liauw、Richard S. Alexander、Robert M. Knabb、Gilbert Lam、Matthew R. Wright、Pancras C. Wong、Ruth R. Wexler

  DOI：10.1021/jm980406a

  日期：1999.7.1

  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.