methyl 4-<2-amino>ethylthio>-2,6-difluorophenoxyacetate | 169298-45-7

• 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: methyl 4-<2-amino>ethylthio>-2,6-difluorophenoxyacetate
• 英文别名: Methyl 2-[4-[2-[(4-chlorophenyl)sulfonyl-[[1-(4-methylphenyl)sulfonylimidazol-4-yl]methyl]amino]ethylsulfanyl]-2,6-difluorophenoxy]acetate
• CAS: 169298-45-7
• 化学式: C₂₈H₂₆ClF₂N₃O₇S₃
• 分子量: 686.178
• InChiKey: QHDMKKAWFVBNHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 4-<2-amino>ethylthio>-2,6-difluorophenoxyacetate 在 1-羟基苯并三唑一水物 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以86%的产率得到methyl 4-<2-ethylthio>-2,6-difluorophenoxyacetate
  参考文献：
  名称：

  Synthesis and evaluation of novel fluorinated sulotroban-related sulfonamide derivatives as thromboxane A2 receptor antagonists

  摘要：

  A series of sulotroban-related arylsulfonamide derivatives possessing a fluorinated phenoxyacetic acid moiety was synthesized and tested for TXA(2) antagonizing ability on U-46619-induced platelet aggregation of rabbit platelet-rich plasma. Introduction of one or more fluorine atoms to the phenoxyacetic acid moiety increased this activity. The most potent compound among these compounds was 10c, which was 40-fold more potent (IC50 3.4 x 10(-7) M) than sulotroban. 10c exhibited high activity (ID50, 0.14 mg/kg) against a U-46619-induced acute thrombocytopenia model in mice when orally administrated. These findings and those of radioligand binding assays with various ligands showed 10c to be a potent and selective systemic TXA, receptor antagonist.

  DOI：

  10.1016/0223-5234(96)88250-x
• 作为产物：
  描述：

  2,6-二氟苯酚 在 盐酸 、 氯磺酸 、 potassium carbonate 、 三苯基膦 、 tin(ll) chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 141.5h， 生成 methyl 4-<2-amino>ethylthio>-2,6-difluorophenoxyacetate
  参考文献：
  名称：

  Synthesis and evaluation of novel fluorinated sulotroban-related sulfonamide derivatives as thromboxane A2 receptor antagonists

  摘要：

  A series of sulotroban-related arylsulfonamide derivatives possessing a fluorinated phenoxyacetic acid moiety was synthesized and tested for TXA(2) antagonizing ability on U-46619-induced platelet aggregation of rabbit platelet-rich plasma. Introduction of one or more fluorine atoms to the phenoxyacetic acid moiety increased this activity. The most potent compound among these compounds was 10c, which was 40-fold more potent (IC50 3.4 x 10(-7) M) than sulotroban. 10c exhibited high activity (ID50, 0.14 mg/kg) against a U-46619-induced acute thrombocytopenia model in mice when orally administrated. These findings and those of radioligand binding assays with various ligands showed 10c to be a potent and selective systemic TXA, receptor antagonist.

  DOI：

  10.1016/0223-5234(96)88250-x