[5-(3-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester | 934176-74-6

• 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-(3-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester
• 英文别名: [5-(3-Nitro-phenyl)-thiophen-2-yl]acetic acid methyl ester；methyl 2-[5-(3-nitrophenyl)thiophen-2-yl]acetate
• CAS: 934176-74-6
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: AYQPHQOQJPAHDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [5-(3-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester 在 palladium on activated charcoal 吡啶 、 lithium hydroxide 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (5-{3-[(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
• 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 作用下， 以 乙醇 、 氯仿 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 90.0h， 生成 [5-(3-nitro-phenyl)-thiophen-2-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Novel Hydroxylated Aromatic Compounds

  摘要：

  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。

  公开号：

  US20080207741A1

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。
• Phloroglucinol derivatives having selectin ligand activity
  申请人：Revotar Biopharmaceuticals AG

  公开号：US08278356B2

  公开（公告）日：2012-10-02

  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.

  含有式(I)中至少一个化合物和药学可接受载体的制药组合物，可用于药物中，其中符号和取代基具有以下含义：例如，-X-为例如，Y为例如或药学可接受的盐，酯或酰胺和前药可应用于调节由E-，P-或选择素结合介导的体外和体内结合过程。
• Hydroxylated aromatic compounds
  申请人：Revotar Biopharmaceuticals AG

  公开号：US07919532B2

  公开（公告）日：2011-04-05

  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.

  药物组合物包含至少一种符号为(I)的化合物和药用可接受载体，适用于药物治疗。其中符号和取代基的含义如下——X——例如为和Y例如为或药用可接受的盐，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 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。