3-(3-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anilino}propyl)benzonitrile | 454437-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(3-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anilino}propyl)benzonitrile
• CAS: 454437-24-2
• 化学式: C₂₆H₃₃N₃O₃
• 分子量: 435.566
• InChiKey: FQBBILAXKGLRHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.59
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(3-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anilino}propyl)benzonitrile 在 吡啶 、 盐酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 157.0h， 生成
  参考文献：
  名称：

  The Discovery of YM-60828: A Potent, Selective and Orally-Bioavailable Factor Xa Inhibitor

  摘要：

  Since Factor Xa (FXa) is well known to play a central role in thrombosis and hemostasis, inhibition of FXa is an attractive target for antithrombotic strategies. As a part of our investigation of a non-peptide, orally available FXa inhibitor, we found that a series of N-[(7-amidino-2-naphthyl)methyl]aniline derivatives possessed potent and selective inhibitory activities. Structure-activity relationship (SAR) of the substituent (R-1) on the central aniline moiety suggested that increasing lipophilicity caused a detrimental effect on anticoagulant activity (prothrombin time assay) in plasma. Several compounds bearing a hydrophilic substituent in R-1 showed not only potent FXa inhibitory activities but also high anticoagulant activities. The best compound in this series was sulfamoylacetic acid derivative 8o (YM-60828) which was a potent, selective and orally bioavailable FXa inhibitor and was chosen for clinical development. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00418-7
• 作为产物：
  描述：

  3-氰基苯甲醛 在 palladium on activated charcoal 氢气 、 三乙酰氧基硼氢化钠 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 39.75h， 生成 3-(3-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anilino}propyl)benzonitrile
  参考文献：
  名称：

  The Discovery of YM-60828: A Potent, Selective and Orally-Bioavailable Factor Xa Inhibitor

  摘要：

  Since Factor Xa (FXa) is well known to play a central role in thrombosis and hemostasis, inhibition of FXa is an attractive target for antithrombotic strategies. As a part of our investigation of a non-peptide, orally available FXa inhibitor, we found that a series of N-[(7-amidino-2-naphthyl)methyl]aniline derivatives possessed potent and selective inhibitory activities. Structure-activity relationship (SAR) of the substituent (R-1) on the central aniline moiety suggested that increasing lipophilicity caused a detrimental effect on anticoagulant activity (prothrombin time assay) in plasma. Several compounds bearing a hydrophilic substituent in R-1 showed not only potent FXa inhibitory activities but also high anticoagulant activities. The best compound in this series was sulfamoylacetic acid derivative 8o (YM-60828) which was a potent, selective and orally bioavailable FXa inhibitor and was chosen for clinical development. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00418-7