(E)-N-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]phenyl}-2-(3-cyanophenyl)ethenesulfonamide | 484065-83-0

• 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: (E)-N-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]phenyl}-2-(3-cyanophenyl)ethenesulfonamide
• CAS: 484065-83-0
• 化学式: C₂₅H₂₉N₃O₅S
• 分子量: 483.588
• InChiKey: TVHHYOZNCYXVIW-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108.73
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-N-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]phenyl}-2-(3-cyanophenyl)ethenesulfonamide 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 3-((E)-2-{Methyl-[4-(piperidin-4-yloxy)-phenyl]-sulfamoyl}-vinyl)-benzamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  Design, synthesis and biological activity of YM-60828 derivatives: potent and orally-Bioavailable factor Xa inhibitors based on naphthoanilide and naphthalensulfonanilide templates

  摘要：

  Factor Xa (FXa) is a serine protease which plays a pivotal role in the coagulation cascade. The inhibition of FXa has received great interest as a potential target for the development of new antithrombotic drug. Herein we describe a series of novel 7-arnidino-2-naphthoanilide and 7-amidino-2-naphthalensulfonanilide derivatives which are potent FXa inhibitors. These scaffolds are rigid and are allowed to adopt an L-shape conformation which was estimated as the active conformation based on a docking study of YM-60828 with FXa. Optimization of the side chain at the central aniline nitrogen of 7-amidino-2-naphthoanilide has led to several potent and orally active FXa inhibitors. 5h (YM-169964), the best compound of these series, showed potent FXa inhibitory activity (IC50 = 3.9 nM) and effectively prolonged prothrombin time by 9.6-fold ex vivo Lit an oral dose of 3 mg/kg in squirrel monkeys. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00106-2
• 作为产物：
  描述：

  4-(4-氨基苯氧基)-1-哌啶甲酸叔丁酯 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (E)-N-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]phenyl}-2-(3-cyanophenyl)ethenesulfonamide
  参考文献：
  名称：

  Design, synthesis and biological activity of YM-60828 derivatives: potent and orally-Bioavailable factor Xa inhibitors based on naphthoanilide and naphthalensulfonanilide templates

  摘要：

  Factor Xa (FXa) is a serine protease which plays a pivotal role in the coagulation cascade. The inhibition of FXa has received great interest as a potential target for the development of new antithrombotic drug. Herein we describe a series of novel 7-arnidino-2-naphthoanilide and 7-amidino-2-naphthalensulfonanilide derivatives which are potent FXa inhibitors. These scaffolds are rigid and are allowed to adopt an L-shape conformation which was estimated as the active conformation based on a docking study of YM-60828 with FXa. Optimization of the side chain at the central aniline nitrogen of 7-amidino-2-naphthoanilide has led to several potent and orally active FXa inhibitors. 5h (YM-169964), the best compound of these series, showed potent FXa inhibitory activity (IC50 = 3.9 nM) and effectively prolonged prothrombin time by 9.6-fold ex vivo Lit an oral dose of 3 mg/kg in squirrel monkeys. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00106-2