tert-butyl (2S)-1-{[4-({[5-(phenylsulfonyl)-2-(trifluoromethyl)phenyl]sulfonyl}amino)piperidin-1-yl-]carbonyl}pyrrolidine-1-carboxylate | 915762-67-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S)-1-{[4-({[5-(phenylsulfonyl)-2-(trifluoromethyl)phenyl]sulfonyl}amino)piperidin-1-yl-]carbonyl}pyrrolidine-1-carboxylate
• 英文别名: 1-Pyrrolidinecarboxylic acid,2-[[4-[[[5-(phenylsulfonyl)-2-(trifluoromethyl)phenyl]sulfonyl]amino]-1-piperidinyl]carbonyl]-,1,1-dimethylethyl ester,(2S)-；tert-butyl (2S)-2-[4-[[5-(benzenesulfonyl)-2-(trifluoromethyl)phenyl]sulfonylamino]piperidine-1-carbonyl]pyrrolidine-1-carboxylate
• CAS: 915762-67-3
• 化学式: C₂₈H₃₄F₃N₃O₇S₂
• 分子量: 645.721
• InChiKey: FCXCNDHEICKHMB-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-1-{[4-({[5-(phenylsulfonyl)-2-(trifluoromethyl)phenyl]sulfonyl}amino)piperidin-1-yl-]carbonyl}pyrrolidine-1-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 5-(phenylsulfonyl)-N-(1-L-prolylpiperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide hydrochloride
  参考文献：
  名称：

  Modulation of Wnt signaling through inhibition of secreted frizzled-related protein I (sFRP-1) with N-substituted piperidinyl diphenylsulfonyl sulfonamides: Part II

  摘要：

  Piperidinyl diphenylsulfonyl sulfonamides are a novel class of molecules that have inhibitory binding affinity for sFRP-1. As a secreted protein sFRP-1 inhibits the function of the secreted Wnt glycoprotein. Therefore, as inhibitors of sFRP-1 these small molecules facilitate the Wnt/beta-catenin canonical signaling pathway. Details of the structure-activity relationships and biological activity of this structural class of compounds will be discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.002
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 5-(phenylsulfonyl)-N-piperidine-4-yl-2-(trifluoromethyl)benzenesulfonamide hydrochloride 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以56%的产率得到tert-butyl (2S)-1-{[4-({[5-(phenylsulfonyl)-2-(trifluoromethyl)phenyl]sulfonyl}amino)piperidin-1-yl-]carbonyl}pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Modulation of Wnt Signaling Through Inhibition of Secreted Frizzled-Related Protein I (sFRP-1) with N-Substituted Piperidinyl Diphenylsulfonyl Sulfonamides

  摘要：

  The diphenylsulfonyl sulfonamide scaffold represented by 1 (WAY-316606) are small molecule inhibitors of the secreted protein sFRP-1, an endogeneous antagonist of the secreted glycoprotein Wnt. Modulators of the Writ pathway have been proposed as anabolic agents for the treatment of osteoporosis or other bone-related disorders. Details of the structure-activity relationships and biological activity from the first structural class of this scaffold will be discussed.

  DOI：

  10.1021/jm801144h

文献信息

• Modulation of Wnt signaling through inhibition of secreted frizzled-related protein I (sFRP-1) with N-substituted piperidinyl diphenylsulfonyl sulfonamides: Part II
  作者：William J. Moore、Jeffrey C. Kern、Ramesh Bhat、Peter V.N. Bodine、Shoichi Fukyama、Girija Krishnamurthy、Ronald L. Magolda、Keith Pitts、Barb Stauffer、Eugene J. Trybulski

  DOI：10.1016/j.bmc.2009.11.002

  日期：2010.1

  Piperidinyl diphenylsulfonyl sulfonamides are a novel class of molecules that have inhibitory binding affinity for sFRP-1. As a secreted protein sFRP-1 inhibits the function of the secreted Wnt glycoprotein. Therefore, as inhibitors of sFRP-1 these small molecules facilitate the Wnt/beta-catenin canonical signaling pathway. Details of the structure-activity relationships and biological activity of this structural class of compounds will be discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Modulation of Wnt Signaling Through Inhibition of Secreted Frizzled-Related Protein I (sFRP-1) with N-Substituted Piperidinyl Diphenylsulfonyl Sulfonamides
  作者：William J. Moore、Jeffrey C. Kern、Ramesh Bhat、Thomas J. Commons、Shoichi Fukayama、Igor Goljer、Girija Krishnamurthy、Ronald L. Magolda、Lisa Nogle、Keith Pitts、Barb Stauffer、Eugene J. Trybulski、Gregory S. Welmaker、Matthew Wilson、Peter V. N. Bodine

  DOI：10.1021/jm801144h

  日期：2009.1.8

  The diphenylsulfonyl sulfonamide scaffold represented by 1 (WAY-316606) are small molecule inhibitors of the secreted protein sFRP-1, an endogeneous antagonist of the secreted glycoprotein Wnt. Modulators of the Writ pathway have been proposed as anabolic agents for the treatment of osteoporosis or other bone-related disorders. Details of the structure-activity relationships and biological activity from the first structural class of this scaffold will be discussed.