5-(2-(5-bromo-1H-indazol-1-yl)ethyl)-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane | 1108184-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 5-(2-(5-bromo-1H-indazol-1-yl)ethyl)-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane
• 英文别名: (1S,4S)-5-[2-(5-bromoindazol-1-yl)ethyl]-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS: 1108184-22-0
• 化学式: C₁₄H₁₆BrN₃O
• 分子量: 322.205
• InChiKey: GIXPUDRXVGQVTP-STQMWFEESA-N

物化性质

• 沸点：
  447.5±35.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-苄氧基-2(1H)-吡啶酮 、 5-(2-(5-bromo-1H-indazol-1-yl)ethyl)-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane 在 copper(l) iodide 、 8-羟基喹啉 作用下， 以 二甲基亚砜 为溶剂， 生成 (S,S)-1-(1-(2-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)ethyl)-1H-indazol-5-yl)-4-(benzyloxy)pyridin-2(1H)-one
  参考文献：
  名称：

  5-(Pyridinon-1-yl)indazoles and 5-(furopyridinon-5-yl)indazoles as MCH-1 antagonists

  摘要：

  A new series of 5-(pyridinon-1-yl)indazoles with MCH-1 antagonist activity were synthesized. Potential cardiovascular risk for these compounds was assessed based upon their interaction with the hERG potassium channel in a mini-patch clamp assay. Selected compounds were studied in a 5-day diet-induced obese mouse model to evaluate their potential use as weight loss agents. Structural modification of the 5-(pyridinon-1-yl) indazoles to give 5-(furopyridinon-5-yl) indazoles provided compounds with enhanced pharmacokinetic properties and improved efficacy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.039
• 作为产物：
  描述：

  (1S,4S)-5-(2-chloroethyl)-2-oxa-5-azabicyclo[2.2.1]heptane 、 5-溴吲唑 以 二甲基亚砜 为溶剂， 生成 5-(2-(5-bromo-1H-indazol-1-yl)ethyl)-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane
  参考文献：
  名称：

  5-(Pyridinon-1-yl)indazoles and 5-(furopyridinon-5-yl)indazoles as MCH-1 antagonists

  摘要：

  A new series of 5-(pyridinon-1-yl)indazoles with MCH-1 antagonist activity were synthesized. Potential cardiovascular risk for these compounds was assessed based upon their interaction with the hERG potassium channel in a mini-patch clamp assay. Selected compounds were studied in a 5-day diet-induced obese mouse model to evaluate their potential use as weight loss agents. Structural modification of the 5-(pyridinon-1-yl) indazoles to give 5-(furopyridinon-5-yl) indazoles provided compounds with enhanced pharmacokinetic properties and improved efficacy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.039

文献信息

• 5-PYRIDINONE SUBSTITUTED INDAZOLES
  申请人：Guzzo Peter

  公开号：US20090082359A1

  公开（公告）日：2009-03-26

  5-pyridinone substituted indazoles of the formula and methods of their use are presented.

  提供了公式为5-吡啶酮取代吲唑并介绍了它们的使用方法。
• 5-pyridinone substituted indazoles
  申请人：Albany Molecular Research, Inc.

  公开号：US08273770B2

  公开（公告）日：2012-09-25

  5-pyridinone substituted indazoles of the formula and methods of their use are presented.

  本文介绍了公式为5-吡啶酮取代的吲唑衍生物及其使用方法。
• 5-pyridinone substituted indazoles and pharmaceutical compositions thereof
  申请人：Albany Molecular Research, Inc.

  公开号：EP2176251B1

  公开（公告）日：2012-02-08
• US8273770B2
  申请人：——

  公开号：US8273770B2

  公开（公告）日：2012-09-25
• 5-(Pyridinon-1-yl)indazoles and 5-(furopyridinon-5-yl)indazoles as MCH-1 antagonists
  作者：Matthew D. Surman、Emily E. Freeman、James F. Grabowski、Mark Hadden、Alan J. Henderson、Guowei Jiang、Xiaowu (May) Jiang、Michele Luche、Yuri Khmelnitsky、Steven Vickers、Jean Viggers、Sharon Cheetham、Peter R. Guzzo

  DOI：10.1016/j.bmcl.2010.09.039

  日期：2010.12

  A new series of 5-(pyridinon-1-yl)indazoles with MCH-1 antagonist activity were synthesized. Potential cardiovascular risk for these compounds was assessed based upon their interaction with the hERG potassium channel in a mini-patch clamp assay. Selected compounds were studied in a 5-day diet-induced obese mouse model to evaluate their potential use as weight loss agents. Structural modification of the 5-(pyridinon-1-yl) indazoles to give 5-(furopyridinon-5-yl) indazoles provided compounds with enhanced pharmacokinetic properties and improved efficacy. (C) 2010 Elsevier Ltd. All rights reserved.