methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate | 218631-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate
• 英文别名: methyl 2-(1,2,4-triazol-1-ylmethyl)prop-2-enoate
• CAS: 218631-60-8
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: MNCBTZFPYYXJAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate 在 盐酸 、 lithium hydroxide 、 sodium hypochlorite 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 14.5h， 生成 3-[5-(2'-Sulfamoyl-biphenyl-4-ylcarbamoyl)-5-[1,2,4]triazol-1-ylmethyl-4,5-dihydro-isoxazol-3-yl]-benzimidic 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
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 2-(溴甲基)丙烯酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate
  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

• Inhibitors of factor Xa with a neutral P1 specificity group
  申请人：——

  公开号：US20030092740A1

  公开（公告）日：2003-05-15

  The present application describes inhibitors of factor Xa with a neutral P1 specificity group of formula I: 1 or pharmaceutically acceptable salt forms thereof, wherein R and E may be groups such as methoxy and halo.

  本申请描述了具有中性P1特异性基团的因子Xa抑制剂，其化学式为I:1或其药学上可接受的盐形式，其中R和E可以是甲氧基和卤素等基团。
• US5998424A
  申请人：——

  公开号：US5998424A

  公开（公告）日：1999-12-07
• US6403620B1
  申请人：——

  公开号：US6403620B1

  公开（公告）日：2002-06-11
• US6602895B2
  申请人：——

  公开号：US6602895B2

  公开（公告）日：2003-08-05