Synthesis of (2-amino)ethyl derivatives of quercetin 3-O-methyl ether and their antioxidant and neuroprotective effects

Bioorg Med Chem. 2015 Aug 1;23(15):4970-4979. doi: 10.1016/j.bmc.2015.05.023. Epub 2015 May 21.

Abstract

Reactive oxygen species have been implicated in several diseases, particularly in ischemia-reperfusion injury. Quercetin 3-O-methyl ether has been reported to show potent antioxidant and neuroprotective activity against neuronal damage induced by reactive oxygen species. Several aminoethyl-substituted derivatives of quercetin 3-O-methyl ether have been synthesized to increase water solubility while retaining antioxidant and neuroprotective activity. Among such derivatives, compound 3a shows potent and well-balanced antioxidant activity in three types of cell-free assay systems and has in vivo neuroprotective effects on transient focal ischemic injury induced by the occlusion of the middle cerebral artery in rats.

Keywords: Aminoethyl; Antioxidant; MCAO model; Neuroprotection; Quercetin 3-O-methyl ether.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis*
  • Antioxidants / pharmacology
  • Antioxidants / therapeutic use
  • Brain / metabolism
  • Brain / pathology
  • Disease Models, Animal
  • Infarction, Middle Cerebral Artery / drug therapy
  • Lipid Peroxidation / drug effects
  • Male
  • Neuroprotective Agents / chemical synthesis*
  • Neuroprotective Agents / pharmacology
  • Neuroprotective Agents / therapeutic use
  • Quercetin / analogs & derivatives*
  • Quercetin / chemistry
  • Quercetin / pharmacology
  • Quercetin / therapeutic use
  • Rats
  • Rats, Sprague-Dawley
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship

Substances

  • Antioxidants
  • Neuroprotective Agents
  • Reactive Oxygen Species
  • quercetin 3-O-methyl ether
  • Quercetin