3-(2,2-difluoro-2-((2R,3S,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamido)benzoic acid | 1224632-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2,2-difluoro-2-((2R,3S,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamido)benzoic acid
• 英文别名: 3-[[2,2-difluoro-2-[(2R,3S,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]acetyl]amino]benzoic acid
• CAS: 1224632-61-4
• 化学式: C₁₅H₁₇F₂NO₉
• 分子量: 393.298
• InChiKey: WYFXXLTZGQGLLG-QMUJVDTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 10% palladium on carbon 、 氢气 作用下， 以100%的产率得到3-(2,2-difluoro-2-((2R,3S,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamido)benzoic acid
  参考文献：
  名称：

  Synthesis of fluorinated C-mannopeptides as sialyl Lewisx mimics for E- and P-selectin inhibition

  摘要：

  The synthesis of fluorinated C-mannopeptides and their evaluation as E- and P-selectin inhibitors is described. These molecules are difluorinated analogues of CH2-glycopeptides already reported to act as sLe(x) mimics. The alpha and beta anomers of these CF2-glycopeptides have been prepared, as well as their 1-hydroxy analogues which were present in solution as an equilibrium mixture of alpha- and beta-pyranose and alpha- and beta-furanose forms. These molecules showed inhibitory activities comparable to their CH2 counterparts with a moderate influence of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.141

文献信息

• Synthesis of fluorinated C-mannopeptides as sialyl Lewisx mimics for E- and P-selectin inhibition
  作者：Vanessa Gouge-Ibert、Camille Pierry、Florent Poulain、Anne-Lise Serre、Céline Largeau、Virginie Escriou、Daniel Scherman、Philippe Jubault、Jean-Charles Quirion、Eric Leclerc

  DOI：10.1016/j.bmcl.2010.01.141

  日期：2010.3

  The synthesis of fluorinated C-mannopeptides and their evaluation as E- and P-selectin inhibitors is described. These molecules are difluorinated analogues of CH2-glycopeptides already reported to act as sLe(x) mimics. The alpha and beta anomers of these CF2-glycopeptides have been prepared, as well as their 1-hydroxy analogues which were present in solution as an equilibrium mixture of alpha- and beta-pyranose and alpha- and beta-furanose forms. These molecules showed inhibitory activities comparable to their CH2 counterparts with a moderate influence of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.