5-(2-acetylphenyl)-2-ethylthiophene-3-carboxylic acid | 1334598-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2-acetylphenyl)-2-ethylthiophene-3-carboxylic acid
• CAS: 1334598-66-1
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: SPTOJKBTJZKBDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 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：
  0.2
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,5,6,7-四氢苯并噻唑-2-胺 、 5-(2-acetylphenyl)-2-ethylthiophene-3-carboxylic acid 在 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-(2-acetylphenyl)-2-ethyl-N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)thiophene-3-carboxamide
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128
• 作为产物：
  描述：

  2-甲基-3-噻吩甲酸 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 硫酸 、 水 、 sodium carbonate 、 溶剂黄146 、 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-(2-acetylphenyl)-2-ethylthiophene-3-carboxylic acid
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128