2-[2-(3-氟-4-羟基-苯基硫烷基)-乙基]-异吲哚-1,3-二酮 | 1026035-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-[2-(3-氟-4-羟基-苯基硫烷基)-乙基]-异吲哚-1,3-二酮
• 英文名称: 2-[2-(3-Fluoro-4-hydroxyphenyl)sulfanylethyl]isoindole-1,3-dione
• CAS: 1026035-62-0
• 化学式: C₁₆H₁₂FNO₃S
• 分子量: 317.341
• InChiKey: SVFWBRVHCOIKAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-(3-氟-4-羟基-苯基硫烷基)-乙基]-异吲哚-1,3-二酮 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Ethyl 2-[4-(2-aminoethylsulfanyl)-2-fluorophenoxy]acetate
  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 、 potassium carbonate 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-[2-(3-氟-4-羟基-苯基硫烷基)-乙基]-异吲哚-1,3-二酮
  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

文献信息

• Synthesis and evaluation of novel fluorinated sulotroban-related sulfonamide derivatives as thromboxane A2 receptor antagonists
  作者：M Sato、Y Kawashima、J Goto、Y Yamane、Y Chiba、S Jinno、M Satake、C Iwata

  DOI：10.1016/0223-5234(96)88250-x

  日期：1995.1

  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.