methyl 2-thiophen-2-yl-benzoxazole-6-carboxylate | 1346701-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: methyl 2-thiophen-2-yl-benzoxazole-6-carboxylate
• 英文别名: methyl 2-thiophen-2-yl-1,3-benzoxazole-6-carboxylate
• CAS: 1346701-28-7
• 化学式: C₁₃H₉NO₃S
• 分子量: 259.285
• InChiKey: POXRHLLCEIIQDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-thiophen-2-yl-benzoxazole-6-carboxylate 在 chromium dichloride 、 nickel dichloride manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 ethyl (E)-4-hydroxy-4-(2-thiophen-2-yl-benzoxazol-6-yl)-but-2-enoate
  参考文献：
  名称：

  [EN] PYRIDAZINONES AS GPR119 AGONISTS
  [FR] PYRIDAZINONES UTILISÉS COMME AGONISTES DU RÉCEPTEUR GPR-119

  摘要：

  公开号：

  WO2011138427A3
• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 methyl 2-thiophen-2-yl-benzoxazole-6-carboxylate
  参考文献：
  名称：

  Structure-based inhibition of acetylcholinesterase and butyrylcholinesterase with 2-Aryl-6-carboxamide benzoxazole derivatives: synthesis, enzymatic assay, and in silico studies

  摘要：

  An important research topic is the discovery of multifunctional compounds targeting different disease-causing components. This research aimed to design and synthesize a series of 2-aryl-6-carboxamide benzoxazole derivatives that inhibit cholinesterases on both the peripheral anionic and catalytic anionic sides. Compounds (7–48) were prepared from 4-amino-3-hydroxybenzoic acid in three steps. The Ellman test, molecular docking with Maestro, and molecular dynamics simulation studies with Desmond were done (Schrodinger, 12.8.117). Compound 36, the most potent compound among the 42 new compounds synthesized, had an inhibitory concentration of IC50 12.62 nM for AChE and IC50 25.45 nM for BChE (whereas donepezil was 69.3 nM and 63.0 nM, respectively). Additionally, compound 36 had docking values ​​of − 7.29 kcal/mol for AChE and − 6.71 kcal/mol for BChE (whereas donepezil was − 6.49 kcal/mol and − 5.057 kcal/mol, respectively). Furthermore, molecular dynamics simulations revealed that compound 36 is stable in the active gorges of both AChE (average RMSD: 1.98 Å) and BChE (average RMSD: 2.2 Å) (donepezil had average RMSD: 1.65 Å and 2.7 Å, respectively). The results show that compound 36 is a potent, selective, mixed-type dual inhibitor of both acetylcholinesterase and butyrylcholinesterase. It does this by binding to both the catalytically active and peripheral anionic sites of cholinesterases at the same time. These findings show that target compounds may be useful for establishing the structural basis for new anti-Alzheimer agents. Graphical abstract

  DOI：

  10.1007/s11030-024-10828-6

文献信息

• Benzoxazole- and tetrahydrobenzoxazole-substituted pyridazinones as GPR119 agonists
  申请人：Grauert Matthias

  公开号：US08772323B2

  公开（公告）日：2014-07-08

  The present invention relates to pyridazinone derivatives of general formula I, wherein the groups A, G and R1 are as defined in the application, the tautomers thereof, stereoisomers thereof, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, and in particular bind to the GPR119 receptor and modulate its activity.

  本发明涉及一般式I的吡啶并咪唑酮衍生物，其中A、G和R1基团如申请中所定义，其互变异构体、立体异构体、混合物和盐具有有价值的药理特性，特别是与GPR119受体结合并调节其活性。
• PYRIDAZINONES AS GPR119 AGONISTS
  申请人：Grauert Matthias

  公开号：US20130172323A1

  公开（公告）日：2013-07-04

  The present invention relates to pyridazinone derivatives of general formula I, wherein the groups A, G and R 1 are as defined in the application, the tautomers thereof, stereoisomers thereof, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, and in particular bind to the GPR119 receptor and modulate its activity.

  本发明涉及一般式I的吡啶并咪唑酮衍生物，其中A、G和R1基团如本申请中所定义，其互变异构体、立体异构体、其混合物和其盐，具有有价值的药理特性，特别是能够结合GPR119受体并调节其活性。
• US8772323B2
  申请人：——

  公开号：US8772323B2

  公开（公告）日：2014-07-08