Green synthesis of novel spiro-indenoquinoxaline derivatives and their cholinesterases inhibition activity

Bioorg Med Chem. 2017 Apr 1;25(7):2057-2064. doi: 10.1016/j.bmc.2017.02.017. Epub 2017 Feb 12.

Abstract

A convenient synthesis of substituted spiroindenoquinoxalines at mild and green conditions was developed. Multicomponent reaction of substituted phenylene diamines, ninhydrin, malononitrile and N,N'-substituted-2-nitroethene-1,1-diamines produced the target compounds. Twelve new spiroindenoquinoxalines were obtained, and their ability in inhibition of acetyl and butyrylcholinesterases were investigated both in vitro and in silico. All compounds showed moderate level activity against both acetyl and butyrylcholinesterases.

Keywords: Acetylcholinesterase inhibition; Butyrylcholinesterase inhibition; Catalyst-free; Indenoquinoxaline; Multi-component reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / drug effects
  • Butyrylcholinesterase / drug effects
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology*
  • Hep G2 Cells
  • Humans
  • Proton Magnetic Resonance Spectroscopy
  • Quinoxalines / chemical synthesis*
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Spectrophotometry, Infrared

Substances

  • Cholinesterase Inhibitors
  • Quinoxalines
  • Acetylcholinesterase
  • Butyrylcholinesterase