N-(3-azidopropyl)-5-(trifluoromethyl)-1-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-4-carboxamide | 1025873-47-5

• 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: N-(3-azidopropyl)-5-(trifluoromethyl)-1-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-4-carboxamide
• CAS: 1025873-47-5
• 化学式: C₁₈H₁₃F₆N₇OS
• 分子量: 489.404
• InChiKey: JKUVLVSKIUWJPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(3-azidopropyl)-5-(trifluoromethyl)-1-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-4-carboxamide 在 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到2-<4-<(3-aminopropyl)carbamoyl>-5-(trifluoromethyl)pyrazol-1-yl>-4-<3-(trifluoromethyl)phenyl>thiazole
  参考文献：
  名称：

  Novel Thiazole-Based Heterocycles as Selective Inhibitors of Fibrinogen-Mediated Platelet Aggregation

  摘要：

  The synthesis and biological activity of novel thiazole-based heterocycles as inhibitors of thrombin-induced human platelet aggregation are described. Further evaluation of selected compounds show they inhibit platelet aggregation as stimulated by a variety of agonists. The more active compounds also were found to inhibit fibrinogen binding to platelets. To further delineate the mechanism of action of these compounds, direct binding studies with the purified glycoprotein (GP) IIb/IIIa receptor were performed. Flow cytometry analyses of 24 and 32 indicate that these compounds block the activation process of the GPIIb/IIIa receptor without denaturing the integrin receptor. On the basis of these studies, 32 exhibited the best profile as a novel nonpeptide inhibitor of fibrinogen-mediated platelet aggregation.

  DOI：

  10.1021/jm00001a008
• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 氢氧化钾 、 sodium azide 、 溴 、 N,N'-羰基二咪唑 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 N-(3-azidopropyl)-5-(trifluoromethyl)-1-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-4-carboxamide
  参考文献：
  名称：

  Novel Thiazole-Based Heterocycles as Selective Inhibitors of Fibrinogen-Mediated Platelet Aggregation

  摘要：

  The synthesis and biological activity of novel thiazole-based heterocycles as inhibitors of thrombin-induced human platelet aggregation are described. Further evaluation of selected compounds show they inhibit platelet aggregation as stimulated by a variety of agonists. The more active compounds also were found to inhibit fibrinogen binding to platelets. To further delineate the mechanism of action of these compounds, direct binding studies with the purified glycoprotein (GP) IIb/IIIa receptor were performed. Flow cytometry analyses of 24 and 32 indicate that these compounds block the activation process of the GPIIb/IIIa receptor without denaturing the integrin receptor. On the basis of these studies, 32 exhibited the best profile as a novel nonpeptide inhibitor of fibrinogen-mediated platelet aggregation.

  DOI：

  10.1021/jm00001a008