methyl 2-(ethylthiomethyl)acrylate | 56750-74-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(ethylthiomethyl)acrylate
• 英文别名: Methyl 2-(ethylsulfanylmethyl)prop-2-enoate
• CAS: 56750-74-4
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: NSAJLMDUUKZCES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(ethylthiomethyl)acrylate 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-(3-cyanophenyl)-5-(ethylthiomethyl)isoxazoline-5-carboxylic acod
  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 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 methyl 2-(ethylthiomethyl)acrylate
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR PROTEIN LABELING, MODIFICATION, ANALYSIS, AND TARGETED DELIVERY
  [FR] COMPOSITIONS ET PROCÉDÉS POUR LE MARQUAGE, LA MODIFICATION, L'ANALYSE ET LA DÉLIVRANCE CIBLÉE DE PROTÉINES

  摘要：

  该发明涉及化学反应性和/或生物活性化合物、试剂及其组合物。更具体地，该发明提供了在化学合成、功能化、传递、探测和/或小分子药物、蛋白质、抗体和其他生物分子的分析测量中有用的新型试剂。该发明提供了作为诊断或治疗用途的新型生物活性剂，以及相关的组合物和使用方法。

  公开号：

  WO2020006340A1

文献信息

• [EN] COMPOSITIONS AND METHODS FOR PROTEIN LABELING, MODIFICATION, ANALYSIS, AND TARGETED DELIVERY<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE MARQUAGE, LA MODIFICATION, L'ANALYSE ET LA DÉLIVRANCE CIBLÉE DE PROTÉINES
  申请人：UNIV MASSACHUSETTS

  公开号：WO2020006340A1

  公开（公告）日：2020-01-02

  The invention relates to chemically reactive and/or biologically active compounds, reagents and compositions thereof. More particularly, the invention provides novel reagents that are useful in chemical synthesis, functionalization, delivery, probing and/or analytical measurements of small molecule drugs, proteins, antibodies and other biomolecules. The invention provides novel biologically active agents useful as diagnostics or therapeutics, and related composition and methods of uses thereof.

  该发明涉及化学反应性和/或生物活性化合物、试剂及其组合物。更具体地，该发明提供了在化学合成、功能化、传递、探测和/或小分子药物、蛋白质、抗体和其他生物分子的分析测量中有用的新型试剂。该发明提供了作为诊断或治疗用途的新型生物活性剂，以及相关的组合物和使用方法。
• 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.