2-(3-cyanophenyl)-N-{4-[(4-piperidyl)oxy]phenyl}ethanesulfonamide | 484065-65-8

• 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: 2-(3-cyanophenyl)-N-{4-[(4-piperidyl)oxy]phenyl}ethanesulfonamide
• CAS: 484065-65-8
• 化学式: C₂₀H₂₃N₃O₃S
• 分子量: 385.487
• InChiKey: NQNTVNKJNQXYPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  91.22
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(3-cyanophenyl)-N-{4-[(4-piperidyl)oxy]phenyl}ethanesulfonamide 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 72.0h， 生成 3-(2-{4-[1-(1-Imino-ethyl)-piperidin-4-yloxy]-phenylsulfamoyl}-ethyl)-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：

  2-(3-氰基苯基)乙醇 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 、 sodium sulfite 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 93.0h， 生成 2-(3-cyanophenyl)-N-{4-[(4-piperidyl)oxy]phenyl}ethanesulfonamide
  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