One-pot green synthesis of 1,3,5-triarylpentane-1,5-dione and triarylmethane derivatives as a new class of tyrosinase inhibitors

Bioorg Med Chem Lett. 2016 Feb 1;26(3):795-798. doi: 10.1016/j.bmcl.2015.12.092. Epub 2015 Dec 28.

Abstract

A new method was developed for one-pot green synthesis 1,3,5-triarylpentane-1,5-dione, triarylmethane, and flavonoid derivatives from the reaction between 2,4-dihydroxybenzaldehyde and hydroxyacetophenones via Aldol, Michael, and Friedel-Crafts additions using boric acid as catalyst in polyethylene glycol 400. The synthetic compounds demonstrated significant tyrosinase inhibitory activities much stronger than that of kojic acid. More important, 1,3,5-triarylpentane-1,5-dione and triarylmethane derivatives were found to be a new class of tyrosinase inhibitors.

Keywords: 1,5-Dione derivative; Boric acid; One-pot green synthesis; Triarylmethane derivative; Tyrosinase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boric Acids / chemistry
  • Catalysis
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Green Chemistry Technology
  • Inhibitory Concentration 50
  • Methane / analogs & derivatives
  • Methane / chemical synthesis
  • Methane / metabolism
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Pentanes / chemistry*
  • Polyethylene Glycols / chemistry
  • Substrate Specificity

Substances

  • Boric Acids
  • Enzyme Inhibitors
  • Pentanes
  • Polyethylene Glycols
  • polyethylene glycol 400
  • Monophenol Monooxygenase
  • Methane
  • boric acid