benzyl N-[[(3S)-piperidin-3-yl]methyl]carbamate | 879396-20-0

• 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: benzyl N-[[(3S)-piperidin-3-yl]methyl]carbamate
• CAS: 879396-20-0
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: OQLARKAOVCMSQV-ZDUSSCGKSA-N

物化性质

• 沸点：
  409.2±28.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[[(3S)-piperidin-3-yl]methyl]carbamate 在 palladium on activated charcoal N-乙基吗啉 、 盐酸 、 dowex 、 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (2R)-N-[[(3R)-1-carbamimidoylpiperidin-3-yl]methyl]-3-(1H-indol-3-yl)-2-(naphthalen-2-ylsulfonylamino)propanamide;hydrochloride
  参考文献：
  名称：

  Design and Synthesis of Potent and Highly Selective Thrombin Inhibitors

  摘要：

  Thrombin, a serine protease, plays a central role in the initiation and propagation of thrombotic events. An extensive search for new thrombin inhibitors was performed, using an unconventional approach. Screening of small basic molecules for binding in the recognition pocket of thrombin led to the discovery of (aminoiminomethyl)piperidine (amidinopiperidine) as a weak, but intrinsically selective, thrombin inhibitor. Elaboration of this molecule provided compounds which inhibit thrombin with K-i's in the range of 20-50 nM and with selectivities of 1000-4000 against trypsin. These inhibitor compounds show a new and unexpected, binding mode to thrombin. Modification of the central building block and then of one of the hydrophobic substituents led to the discovery of a new family of thrombin inhibitors which has reverted td the former binding mode to thrombin. This last class of compounds shows inhibitory activities in the picomolar range; low toxicity; and a short plasma half life which favors its use for an intravenous application. From this series of thrombin;inhibitors, 19f (Ro 46-6240) was selected for clinical development as an antithrombotic agent for intravenous administration.

  DOI：

  10.1021/jm00049a008
• 作为产物：
  描述：

  tert-butyl (3S)-3-(methylsulfonyloxymethyl)piperidine-1-carboxylate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium azide 、 氢气 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、1000.0 kPa 条件下， 反应 32.5h， 生成 benzyl N-[[(3S)-piperidin-3-yl]methyl]carbamate
  参考文献：
  名称：

  Design and Synthesis of Potent and Highly Selective Thrombin Inhibitors

  摘要：

  Thrombin, a serine protease, plays a central role in the initiation and propagation of thrombotic events. An extensive search for new thrombin inhibitors was performed, using an unconventional approach. Screening of small basic molecules for binding in the recognition pocket of thrombin led to the discovery of (aminoiminomethyl)piperidine (amidinopiperidine) as a weak, but intrinsically selective, thrombin inhibitor. Elaboration of this molecule provided compounds which inhibit thrombin with K-i's in the range of 20-50 nM and with selectivities of 1000-4000 against trypsin. These inhibitor compounds show a new and unexpected, binding mode to thrombin. Modification of the central building block and then of one of the hydrophobic substituents led to the discovery of a new family of thrombin inhibitors which has reverted td the former binding mode to thrombin. This last class of compounds shows inhibitory activities in the picomolar range; low toxicity; and a short plasma half life which favors its use for an intravenous application. From this series of thrombin;inhibitors, 19f (Ro 46-6240) was selected for clinical development as an antithrombotic agent for intravenous administration.

  DOI：

  10.1021/jm00049a008

文献信息

• Quinazolines useful as modulators of ion channels
  申请人：Wilson Dean

  公开号：US20090312342A1

  公开（公告）日：2009-12-17

  The present invention relates to compounds useful as inhibitors of voltage-gated sodium channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及用作电压门控钠通道抑制剂的化合物。本发明还提供了包含本发明化合物的药学上可接受的组合物，并提供了使用这些组合物治疗各种疾病的方法。
• QUINAZOLINES USEFUL AS MODULATORS OF ION CHANNELS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1784393B1

  公开（公告）日：2009-07-01
• US7928107B2
  申请人：——

  公开号：US7928107B2

  公开（公告）日：2011-04-19
• US8283354B2
  申请人：——

  公开号：US8283354B2

  公开（公告）日：2012-10-09
• Design and Synthesis of Potent and Highly Selective Thrombin Inhibitors
  作者：Kurt Hilpert、Jean Ackermann、David W. Banner、Alain Gast、Klaus Gubernator、Paul Hadvary、Ludvik Labler、Klaus Mueller、Gerard Schmid、Thomas B. Tschopp、Han van de Waterbeemd

  DOI：10.1021/jm00049a008

  日期：1994.11.1

  Thrombin, a serine protease, plays a central role in the initiation and propagation of thrombotic events. An extensive search for new thrombin inhibitors was performed, using an unconventional approach. Screening of small basic molecules for binding in the recognition pocket of thrombin led to the discovery of (aminoiminomethyl)piperidine (amidinopiperidine) as a weak, but intrinsically selective, thrombin inhibitor. Elaboration of this molecule provided compounds which inhibit thrombin with K-i's in the range of 20-50 nM and with selectivities of 1000-4000 against trypsin. These inhibitor compounds show a new and unexpected, binding mode to thrombin. Modification of the central building block and then of one of the hydrophobic substituents led to the discovery of a new family of thrombin inhibitors which has reverted td the former binding mode to thrombin. This last class of compounds shows inhibitory activities in the picomolar range; low toxicity; and a short plasma half life which favors its use for an intravenous application. From this series of thrombin;inhibitors, 19f (Ro 46-6240) was selected for clinical development as an antithrombotic agent for intravenous administration.