5-(2-amino-phenyl)-thiophene-2-carboxylic acid methyl ester | 934176-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(2-amino-phenyl)-thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 5-(2-aminophenyl)thiophene-2-carboxylate
• CAS: 934176-62-2
• 化学式: C₁₂H₁₁NO₂S
• 分子量: 233.291
• InChiKey: XJWKWKIFCJJVII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-amino-phenyl)-thiophene-2-carboxylic acid methyl ester 在 吡啶 、 lithium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 66.0h， 生成 5-{2-[(2',3',4'-trimethoxy-biphenyl-3-carbonyl)-amino]-phenyl}-thiophene-2-carboxylic 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：

  5-溴-2-羧基噻吩 在 四(三苯基膦)钯 硫酸 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 生成 5-(2-amino-phenyl)-thiophene-2-carboxylic 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

文献信息

• Novel Hydroxylated Aromatic Compounds
  申请人：Aydt Ewald M.

  公开号：US20080207741A1

  公开（公告）日：2008-08-28

  Pharmaceutical compositions comprising at least one compound of the formula (I) and a pharmaceutically acceptable carrier which is useful in a medicine wherein the symbols and substituents have the following meaning —X— is e.g. and Y being e.g. or the pharmaceutically acceptable salts, esters or amides and prodrugs can be 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(I)的化合物和药用可接受的载体的药物组合物，在药物中有用 其中符号和取代基具有以下含义 —X— 例如 Y 例如 或者药用可接受的盐、酯或酰胺和前药可以被应用来调节由E-、P-或L-选择素结合介导的体外和体内结合过程。
• NOVEL MULTI-CYCLIC COMPOUNDS
  申请人：Kranich Remo

  公开号：US20090030015A1

  公开（公告）日：2009-01-29

  Pharmaceutical compositions comprising at least one compound of the formulas (Ia) or (Ib) or (IIa) or (IIb) and a pharmaceutically acceptable carrier wherein the symbols and substituents 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.

  药物组合物包括至少一种化合物，化合物的结构式为(Ia)或(Ib)或(IIa)或(IIb)，以及药学上可接受的载体。其中符号和取代基的含义如下：-X-例如，Y可以是例如，或者药学上可接受的盐，可以用于调节由E-、P-或L-选择素介导的体外和体内结合过程。
• Novel Aromatic Nitro Compounds
  申请人：Aydt Ewald M.

  公开号：US20090105280A1

  公开（公告）日：2009-04-23

  Pharmaceutical compositions comprising at least one compound of e.g. the formulas (Ie) and a pharmaceutically acceptable carrier which is useful in a medicine wherein the symbols and substituents have the following meaning —X— is e.g. and Y is e.g. or the pharmaceutically acceptable salts, esters or amides and prodrugs of the above identified compounds 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化合物，例如公式（Ie）中的一种，以及一种药学上可接受的载体，该组成物在药学上有用，其中符号和取代基具有以下含义- X- 例如，Y是例如或上述化合物的药学上可接受的盐，酯或酰胺和前药可用于调节由E，P或L选择素结合介导的体内外结合过程。
• NOVEL AROMATIC NITRO COMPOUNDS
  申请人：AYDT Ewald M.

  公开号：US20110053939A1

  公开（公告）日：2011-03-03

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

  本发明涉及一种含有至少一种化合物的制药组合物，例如公式（Ie）中的化合物，以及一种药用可接受载体，其在药学上有用，其中符号和取代基具有以下含义：X-例如，Y-例如，或上述已识别化合物的药学上可接受的盐，酯或酰胺和前药可以应用于调节E-，P-或L-选择素结合介导的体内外结合过程。
• NOVEL PHLOROGLUCINOL DERIVATIVES HAVING SELECTIN LIGAND ACTIVITY
  申请人：AYDT Ewald M.

  公开号：US20110142765A1

  公开（公告）日：2011-06-16

  Pharmaceutical compositions comprising at least one compound of the formula (I) and a pharmaceutically acceptable carrier which is useful in a medicine wherein the symbols and substituents have the following meaning —X— is e.g. and Y being e.g. or the pharmaceutically acceptable salts, esters or amides and prodrugs can be applied to modulate the in-vitro and in-vivo binding processes mediated by E-, P- or selectin binding.

  制药组合物包括至少一种式(I)化合物和药学上可接受的载体，其在药学上有用，其中符号和取代基具有以下含义：-X-例如，并且Y例如或药学上可接受的盐，酯或酰胺和前药可以应用于调节由E-，P-或选择素结合介导的体外和体内结合过程。