(5-{2-[(2',3',4'-trimethoxy-biphenyl-3-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid | 928847-17-0

• 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-{2-[(2',3',4'-trimethoxy-biphenyl-3-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid
• 英文别名: 2-[5-[2-[[3-(2,3,4-Trimethoxyphenyl)benzoyl]amino]phenyl]thiophen-2-yl]acetic acid
• CAS: 928847-17-0
• 化学式: C₂₈H₂₅NO₆S
• 分子量: 503.576
• InChiKey: PEEXUIMRTXBGJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5-{2-[(2',3',4'-trimethoxy-biphenyl-3-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以110 mg的产率得到(5-{2-[(2',3',4'-Trihydroxy-biphenyl-3-carbonyl)-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：

  3-溴苯甲酸甲酯 在 四(三苯基膦)钯 、 N,N-二甲基甲酰胺 吡啶 、 lithium hydroxide 、 草酰氯 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 (5-{2-[(2',3',4'-trimethoxy-biphenyl-3-carbonyl)-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

文献信息

• Novel aromatic compounds and their use in medical applications
  申请人：Revotar Biopharmaceuticals AG

  公开号：EP1764093A1

  公开（公告）日：2007-03-21

  Pharmaceutical compositions comprising at least one compound of the formulas (Ia) or (Ib) and a pharmaceutically acceptable carrier which is useful in a medicine wherein the symbols and substituents have the following meaning -X- is e.g. or or or and Y being or or the pharmaceutically acceptable salts, esters or amides and prodrugs of the above identified compounds of formulas (Ia) or (Ib). The compounds are applied to modulate the in-vitro and in-vivo binding processes mediated by E-, P- or L-selectin binding.

  含有至少一个式(Ia)或(Ib)化合物和一种药用载体的制药组合物，在药物中有用，其中符号和取代基的含义如下-X-为例如或或或和Y为或或上述式(Ia)或(Ib)化合物的药用盐、酯或酰胺以及前药。这些化合物用于调节由E-、P-或L-选择素结合介导的体外和体内结合过程。
• Novel Aromatic Compounds and Their Use in Medical Applications
  申请人：Aydt Ewald M.

  公开号：US20080207639A1

  公开（公告）日：2008-08-28

  Pharmaceutical compositions comprising at least one compound of the formulas (Ia) or (Ib) and a pharmaceutically acceptable carrier wherein the symbols have the following meaning —X— is e.g. and Y being e.g. or the pharmaceutically acceptable salts can be applied to modulate the in-vitro and in-vivo binding processes mediated by E-, P- or L-selectin binding.

  药物组成物包括至少一种式(Ia)或(Ib)的化合物和药学上可接受的载体，其中符号的含义如下：-X-例如，Y为例如或药学上可接受的盐，可用于调节由E、P或L选择素结合介导的体外和体内结合过程。
• NOVEL AROMATIC COMPOUNDS AND THEIR USE IN MEDICAL APPLICATIONS
  申请人：AYDT Ewald M.

  公开号：US20110152291A1

  公开（公告）日：2011-06-23

  Pharmaceutical compositions comprising at least one compound of the formulas (Ia) or (Ib) and a pharmaceutically acceptable carrier wherein the symbols have the following meaning —X- is e.g. and Y being e.g. or the pharmaceutically acceptable salts can be applied to modulate the in-vitro and in-vivo binding processes mediated by E-, P- or L-selectin binding.

  制药组合物包括至少一种式(Ia)或(Ib)的化合物和一种药学上可接受的载体，其中符号具有以下含义：-X-例如，Y为例如，或药学上可接受的盐可用于调节由E-、P-或L-选择素结合介导的体外和体内结合过程。
• US7923473B2
  申请人：——

  公开号：US7923473B2

  公开（公告）日：2011-04-12
• US8394835B2
  申请人：——

  公开号：US8394835B2

  公开（公告）日：2013-03-12