6-(2-methoxybenzyloxy)-2-cyanobenzothiophene | 1209467-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-(2-methoxybenzyloxy)-2-cyanobenzothiophene
• CAS: 1209467-20-8
• 化学式: C₁₇H₁₃NO₂S
• 分子量: 295.362
• InChiKey: OYFGSBCBRHIPLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(2-methoxybenzyloxy)-2-cyanobenzothiophene 在 lithium hexamethyldisilazane 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以16%的产率得到6-(2-methoxybenzyloxy)benzo[b]thiophene-2-carboxamidine
  参考文献：
  名称：

  Studies of Benzothiophene Template as Potent Factor IXa (FIXa) Inhibitors in Thrombosis

  摘要：

  FIXa is a serine protease enzyme involved in the intrinsic pathway of the coagulation cascade. The upstream intervention of the coagulation cascade in selectively inhibiting FIXa would leave hemostasis Intact via the extrinsic pathway, leading to an optimum combination of efficacy and safety with low incidence of bleeding. We have identified 2-amindinobenzothiophene template as a lead scaffold for FIXa inhibiton based on its homology with urokinase plasminogen activator (uPA). Subsequent SAR work oil the template revealed a number of highly potent FIXa inhibitors, though with moderate selectivity against FXa. X-ray Study with one of the analogues demonstrated active site binding interaction with the induced opening of the S1 beta pocket and a secondary binding at the S2-S4 sites, which is ill direct contrast with the previous finding.

  DOI：

  10.1021/jm901475e
• 作为产物：
  描述：

  6-羟基-2-氰基苯并噻吩 、 2-甲氧基苯甲醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到6-(2-methoxybenzyloxy)-2-cyanobenzothiophene
  参考文献：
  名称：

  Studies of Benzothiophene Template as Potent Factor IXa (FIXa) Inhibitors in Thrombosis

  摘要：

  FIXa is a serine protease enzyme involved in the intrinsic pathway of the coagulation cascade. The upstream intervention of the coagulation cascade in selectively inhibiting FIXa would leave hemostasis Intact via the extrinsic pathway, leading to an optimum combination of efficacy and safety with low incidence of bleeding. We have identified 2-amindinobenzothiophene template as a lead scaffold for FIXa inhibiton based on its homology with urokinase plasminogen activator (uPA). Subsequent SAR work oil the template revealed a number of highly potent FIXa inhibitors, though with moderate selectivity against FXa. X-ray Study with one of the analogues demonstrated active site binding interaction with the induced opening of the S1 beta pocket and a secondary binding at the S2-S4 sites, which is ill direct contrast with the previous finding.

  DOI：

  10.1021/jm901475e