Greener synthesis of indolizine analogues using water as a base and solvent: study for larvicidal activity against Anopheles arabiensis

Chem Biol Drug Des. 2016 Dec;88(6):899-904. doi: 10.1111/cbdd.12823. Epub 2016 Sep 9.

Abstract

Greener synthesis of a series of novel indolizine analogues have been achieved by the cyclization of aromatic cycloimmonium ylides with electron-deficient alkynes in the presence of water as the base and solvent at 80 °C. Yield of the title compounds was good and reactions performed were eco-friendly. The structures of these newly synthesized compounds have been confirmed by spectroscopic techniques such as FTIR, NMR, LC-MS, and elemental analysis. Characterized title compounds were evaluated for larvicidal activity against Anopheles arabiensis by standard WHO larvicidal assay using Temefos as standard at 4 μg/mL. Title compounds 2e, 2f, and 2g emerged as promising larvicidal agents.

Keywords: characterization; indolizine analogues; larvicidal activity; synthesis.

MeSH terms

  • Animals
  • Anopheles / drug effects*
  • Anopheles / growth & development
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Chromatography, Liquid
  • Indolizines / chemical synthesis*
  • Indolizines / pharmacology
  • Larva / drug effects*
  • Proton Magnetic Resonance Spectroscopy
  • Solvents / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry

Substances

  • Indolizines
  • Solvents
  • Water