3'-[2-(benzyloxy)-2-oxoethyl]-1,1'-biphenyl-2-yl 3,4,5-trihydroxybenzoate | 1026692-25-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 3'-[2-(benzyloxy)-2-oxoethyl]-1,1'-biphenyl-2-yl 3,4,5-trihydroxybenzoate
• 英文别名: [2-[3-(2-Oxo-2-phenylmethoxyethyl)phenyl]phenyl] 3,4,5-trihydroxybenzoate
• CAS: 1026692-25-0
• 化学式: C₂₈H₂₂O₇
• 分子量: 470.478
• InChiKey: XSMKFMKZKGXSJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-[2-(benzyloxy)-2-oxoethyl]-1,1'-biphenyl-2-yl 3,4,5-trihydroxybenzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以9 mg的产率得到2-[3-[2-(3,4,5-Trihydroxybenzoyl)oxyphenyl]phenyl]acetic acid
  参考文献：
  名称：

  Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists

  摘要：

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.

  DOI：

  10.1021/jm060536g
• 作为产物：
  描述：

  三乙酰基没食子酰氯 在 ammonium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.83h， 生成 3'-[2-(benzyloxy)-2-oxoethyl]-1,1'-biphenyl-2-yl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists

  摘要：

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.

  DOI：

  10.1021/jm060536g

文献信息

• Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists
  作者：Remo Kranich、Anke S. Busemann、Daniel Bock、Sabine Schroeter-Maas、Diana Beyer、Bo Heinemann、Michael Meyer、Katrin Schierhorn、Rainer Zahlten、Gerhard Wolff、Ewald M. Aydt

  DOI：10.1021/jm060536g

  日期：2007.3.1

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.