[5-(4-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester | 934176-66-6

• 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: [5-(4-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester
• CAS: 934176-66-6
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: HDVMGRYCERNQJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [5-(4-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester 在 palladium on activated charcoal 吡啶 、 lithium hydroxide 、 ammonium formate 、 三溴化硼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-[5-[4-[[3-(2,3,4-Trihydroxyphenyl)benzoyl]amino]phenyl]thiophen-2-yl]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：

  噻吩-2-乙酸甲酯 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 72.0h， 生成 [5-(4-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester
  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