{(S)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine | 603992-48-9

• 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: {(S)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine
• 英文别名: N-[(2S)-2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propyl]pyridin-2-amine
• CAS: 603992-48-9
• 化学式: C₂₀H₂₆N₄O₂
• 分子量: 354.452
• InChiKey: WGNFRNVIFIRYDD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {(S)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 {(S)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine dihydrochloride
  参考文献：
  名称：

  Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines

  摘要：

  通过将式I化合物与NH2R′1反应制备出一种II式的N1-(2′-吡啶基)-1,2-烷二胺磺酸的方法，其中R和R′如规范中定义。该发明还包括II式化合物及其光学异构体。II式化合物是一种中间体，用于制备在5-HT1A受体上活性的手性哌嗪衍生物。

  公开号：

  US20030204087A1
• 作为产物：
  描述：

  (R)-4,5-dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]-oxathiazole-2,2-dioxide 、 1-(2,3-二氢-1,4-苯并二烷-5-基)哌嗪盐酸盐 在 potassium carbonate 、 盐酸 作用下， 以 乙腈 为溶剂， 反应 78.0h， 以70%的产率得到{(S)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Benzodioxanylpiperazine Derivatives as Potent Serotonin 5-HT_1A Antagonists:  The Discovery of Lecozotan

  摘要：

  A series of benzodioxanylpiperazine derivatives possessing a 4-aryl amide substituent was prepared and evaluated for 5-HT1A affinity and functional antagonist activity in vitro and in vivo. All of the compounds in this series possessed high affinity for the human 5-HT1A receptor and many displayed potent antagonist activity in vitro and varying degrees of intrinsic activity in vivo. Compound 11c (Lecozotan) was selected for further development and is currently in clinical trials.

  DOI：

  10.1021/jm049493z

文献信息

• PREPARATION OF N1-(2'-PYRIDYL)-1,2-PROPANEDIAMINE SULFAMIC ACID AND ITS USE IN THE SYNTHESIS OF BIOLOGICALLY ACTIVE PIPERAZINES
  申请人：Wyeth

  公开号：EP1483243B1

  公开（公告）日：2007-04-18
• US7361773B2
  申请人：——

  公开号：US7361773B2

  公开（公告）日：2008-04-22
• Synthesis and Biological Evaluation of Benzodioxanylpiperazine Derivatives as Potent Serotonin 5-HT_1A Antagonists:  The Discovery of Lecozotan
  作者：Wayne E. Childers,、Magid A. Abou-Gharbia、Michael G. Kelly、Terrance H. Andree、Boyd L. Harrison、Douglas M. Ho、Geoffrey Hornby、Donna M. Huryn、Lisa Potestio、Sharon J. Rosenzweig-Lipson、Jean Schmid、Deborah L. Smith、Stacey J. Sukoff、Gan Zhang、Lee E. Schechter

  DOI：10.1021/jm049493z

  日期：2005.5.1

  A series of benzodioxanylpiperazine derivatives possessing a 4-aryl amide substituent was prepared and evaluated for 5-HT1A affinity and functional antagonist activity in vitro and in vivo. All of the compounds in this series possessed high affinity for the human 5-HT1A receptor and many displayed potent antagonist activity in vitro and varying degrees of intrinsic activity in vivo. Compound 11c (Lecozotan) was selected for further development and is currently in clinical trials.
• Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines
  申请人：Wyeth

  公开号：US20030204087A1

  公开（公告）日：2003-10-30

  A process for making an N1-(2′-pyridyl)-1,2-alkanediamine sulfamic acid of formula II by reacting a compound of formula I with NH 2 R′ 1 wherein R and R′ are as defined in the specification. The invention also includes the compound of formula II, and optical isomers thereof. The compound of formula II is an intermediate useful for making chiral piperazine derivatives which are active at the 5-HT 1A receptor.

  通过将式I化合物与NH2R′1反应制备出一种II式的N1-(2′-吡啶基)-1,2-烷二胺磺酸的方法，其中R和R′如规范中定义。该发明还包括II式化合物及其光学异构体。II式化合物是一种中间体，用于制备在5-HT1A受体上活性的手性哌嗪衍生物。