6-Hydroxy-2-oxochromene-3-carbonyl chloride | 72973-51-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-Hydroxy-2-oxochromene-3-carbonyl chloride
• CAS: 72973-51-4
• 化学式: C₁₀H₅ClO₄
• 分子量: 224.6
• InChiKey: GICIJDLABNIVCS-UHFFFAOYSA-N

物化性质

• 沸点：
  464.2±45.0 °C(Predicted)
• 密度：
  1.608±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-2-oxochromene-3-carbonyl chloride 、 4-(2-氨基乙基)-1-苄基哌啶 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 N-[2-(1-benzylpiperidin-4-yl)ethyl]-6-hydroxy-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

  摘要：

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.024
• 作为产物：
  描述：

  7-羟基香豆素-3-羧酸 在 氯化亚砜 作用下， 生成 6-Hydroxy-2-oxochromene-3-carbonyl chloride
  参考文献：
  名称：

  Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

  摘要：

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.024

文献信息

• Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
  作者：Franco Chimenti、Bruna Bizzarri、Adriana Bolasco、Daniela Secci、Paola Chimenti、Arianna Granese、Simone Carradori、Daniela Rivanera、Alessandra Zicari、M. Maddalena Scaltrito、Francesca Sisto

  DOI：10.1016/j.bmcl.2010.06.048

  日期：2010.8

  N-substituted-3-carboxamido-coumarin derivatives were prepared and evaluated for selective antibacterial activity against 20 isolates of Helicobacter pylori clinical strains, including five metronidazole resistant ones. Some of them possessed the best activity against H. pylori metronidazole resistant strains with MIC values lower than the drug reference (metronidazole). Furthermore, anti-inflammatory activity through the inhibition of the IL-8 production was investigated. (c) 2010 Elsevier Ltd. All rights reserved.
• US4159268A
  申请人：——

  公开号：US4159268A

  公开（公告）日：1979-06-26