methyl 2-bromo-4-<2-(4-chlorophenylsulfonylamino)ethylthio>-6-fluorophenoxyacetate | 151389-51-4

• 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 2-bromo-4-<2-(4-chlorophenylsulfonylamino)ethylthio>-6-fluorophenoxyacetate
• 英文别名: Methyl 2-[2-bromo-4-[2-[(4-chlorophenyl)sulfonylamino]ethylsulfanyl]-6-fluorophenoxy]acetate
• CAS: 151389-51-4
• 化学式: C₁₇H₁₆BrClFNO₅S₂
• 分子量: 512.805
• InChiKey: PDEVXJFJLYVYJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-4-<2-(4-chlorophenylsulfonylamino)ethylthio>-6-fluorophenoxyacetate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以88%的产率得到2-bromo-4-<2-(4-chlorophenylsulfonylamino)ethylthio>-6-fluorophenoxyacetic acid
  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-氟苯酚 在 氯磺酸 、 硫酸 、 溴 、 potassium carbonate 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 25.83h， 生成 methyl 2-bromo-4-<2-(4-chlorophenylsulfonylamino)ethylthio>-6-fluorophenoxyacetate
  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