(2R,3R)-3-(piperazin-1-yl)butan-2-ol | 954138-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2R,3R)-3-(piperazin-1-yl)butan-2-ol
• 英文别名: (I+/-R,I(2)R)-I+/-,I(2)-Dimethyl-1-piperazineethanol；(2R,3R)-3-piperazin-1-ylbutan-2-ol
• CAS: 954138-58-0
• 化学式: C₈H₁₈N₂O
• 分子量: 158.244
• InChiKey: LEDOWOUNDKUKOQ-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7-dichloro-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one 、 (2R,3R)-3-(piperazin-1-yl)butan-2-ol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 7-chloro-3-[4-[(2R,3R)-3-hydroxybutan-2-yl]piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 3-[4-(2-Hydroxyethyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one, a Potent, Orally Active, Brain Penetrant Inhibitor of Phosphodiesterase 5 (PDE5)

  摘要：

  We recently described a novel series of aminopyridopyrazinones as PDE5 inhibitors. Efforts toward optimization of this series culminated in the identification of 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)- 1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one, which possessed an excellent potency and selectivity profile and demonstrated robust in vivo blood pressure lowering in a spontaneously hypertensive rat (SHR) model. Furthermore, this compound is brain penetrant and will be a useful agent for evaluating the therapeutic potential of central inhibition of PDE5. This compound has recently entered clinical trials.

  DOI：

  10.1021/jm901781q

文献信息

• Pyridine [3,4-b] Pyrazinones
  申请人：Hughes O. Robert

  公开号：US20070249615A1

  公开（公告）日：2007-10-25

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I: wherein R 2 , R 6A , R 6B and R 8 are as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, synthetic methods, and intermediates are also disclosed.

  本文披露了化合物及其药用可接受的盐，其中化合物具有以下结构的Formula I：其中R2、R6A、R6B和R8如规范中定义。同时还披露了相应的药物组合物、治疗方法、合成方法和中间体。
• PYRIDIN[3,4-B]PYRAZINONES
  申请人：Pfizer Products Inc.

  公开号：EP2013208B1

  公开（公告）日：2011-06-22
• US7902195B2
  申请人：——

  公开号：US7902195B2

  公开（公告）日：2011-03-08
• [EN] PYRIDINE[3,4-B]PYRAZINONES<br/>[FR] PYRIDINE[3,4-B]PYRAZINONES
  申请人：PFIZER PROD INC

  公开号：WO2007122466A1

  公开（公告）日：2007-11-01

  [EN] Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I: wherein R², R^6?, R^6B and R⁸ are as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, synthetic methods, and intermediates are also disclosed.
  [FR] L'invention concerne des composés et des sels de ceux-ci pharmaceutiquement acceptables. Lesdits composés sont représentés par la formule (I), dans laquelle R², R^6?, R^6B et R⁸ sont tels que définis dans la spécification. L'invention concerne également des compositions pharmaceutiques correspondantes, des méthodes de traitement, des procédés de synthèse et des intermédiaires.
• Design, Synthesis, and Biological Evaluation of 3-[4-(2-Hydroxyethyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-<i>b</i>]pyrazin-2(1<i>H</i>)-one, a Potent, Orally Active, Brain Penetrant Inhibitor of Phosphodiesterase 5 (PDE5)
  作者：Robert O. Hughes、D. Joseph Rogier、E. Jon Jacobsen、John K. Walker、Alan MacInnes、Brian R. Bond、Lena L. Zhang、Ying Yu、Yi Zheng、Jeanne M. Rumsey、Jennie L. Walgren、Sandra W. Curtiss、Yvette M. Fobian、Steven E. Heasley、Jerry W. Cubbage、Joseph B. Moon、David L. Brown、Brad A. Acker、Todd M. Maddux、Mike B. Tollefson、Brent V. Mischke、Dafydd R. Owen、John N. Freskos、John M. Molyneaux、Alan G. Benson、Rhadika M. Blevis-Bal

  DOI：10.1021/jm901781q

  日期：2010.3.25

  We recently described a novel series of aminopyridopyrazinones as PDE5 inhibitors. Efforts toward optimization of this series culminated in the identification of 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)- 1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one, which possessed an excellent potency and selectivity profile and demonstrated robust in vivo blood pressure lowering in a spontaneously hypertensive rat (SHR) model. Furthermore, this compound is brain penetrant and will be a useful agent for evaluating the therapeutic potential of central inhibition of PDE5. This compound has recently entered clinical trials.