3-[4-[(2S)-3-hydroxy-2-[(4-naphthalen-2-ylpyrimidin-2-yl)amino]propyl]imidazol-1-yl]propanenitrile | 1207452-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[4-[(2S)-3-hydroxy-2-[(4-naphthalen-2-ylpyrimidin-2-yl)amino]propyl]imidazol-1-yl]propanenitrile
• CAS: 1207452-55-8
• 化学式: C₂₃H₂₂N₆O
• 分子量: 398.467
• InChiKey: QJHOKNYENMWWCP-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴丙腈 、 (2S)-3-(1H-imidazol-4-yl)-2-{[4-(2-naphthyl)pyrimidin-2-yl]amino}propan-1-ol 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 3-[4-[(2S)-3-hydroxy-2-[(4-naphthalen-2-ylpyrimidin-2-yl)amino]propyl]imidazol-1-yl]propanenitrile
  参考文献：
  名称：

  Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system

  摘要：

  A series of (hetero)arylpyrimidines agonists of the Wnt-beta-catenin cellular messaging system have been prepared. These compounds show activity in U2OS cells transfected with Wnt-3 alpha, TCF-luciferase, Dkk-1 and tk-Renilla. Selected compounds show minimal GSK-3 beta inhibition indicating that the Wnt-beta-catenin agonism activity most likely comes from interaction at Wnt-3 alpha/Dkk-1. Two examples 1 and 25 show in vivo osteogenic activity in a mouse calvaria model. One example 1 is shown to activate non-phosphorylated beta-catenin formation in bone. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.093

文献信息

• Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system
  作者：Adam M. Gilbert、Matthew G. Bursavich、Nippa Alon、Bheem M. Bhat、Frederick J. Bex、Michael Cain、Valerie Coleburn、Virginia Gironda、Paula Green、Diane B. Hauze、Yogendra Kharode、Girija Krishnamurthy、Matthew Kirisits、Ho-Sun Lam、Yao-Bin Liu、Sabrina Lombardi、Jeanne Matteo、Richard Murrills、John A. Robinson、Sally Selim、Michael Sharp、Raymond Unwalla、Usha Varadarajan、Weiguang Zhao、Paul J. Yaworsky

  DOI：10.1016/j.bmcl.2009.10.093

  日期：2010.1

  A series of (hetero)arylpyrimidines agonists of the Wnt-beta-catenin cellular messaging system have been prepared. These compounds show activity in U2OS cells transfected with Wnt-3 alpha, TCF-luciferase, Dkk-1 and tk-Renilla. Selected compounds show minimal GSK-3 beta inhibition indicating that the Wnt-beta-catenin agonism activity most likely comes from interaction at Wnt-3 alpha/Dkk-1. Two examples 1 and 25 show in vivo osteogenic activity in a mouse calvaria model. One example 1 is shown to activate non-phosphorylated beta-catenin formation in bone. (C) 2009 Elsevier Ltd. All rights reserved.