Synthesis and theoretical calculations of carbazole substituted chalcone urea derivatives and studies their polyphenol oxidase enzyme activity

J Enzyme Inhib Med Chem. 2013 Aug;28(4):808-15. doi: 10.3109/14756366.2012.688040. Epub 2012 Jul 18.

Abstract

Synthesis of carbazole substituted chalcone urea derivatives and their polyphenol oxidase enzyme activity effects on the diphenolase activity of banana tyrosinase were evaluated. Tyrosinase has been purified from banana on an affinity gel comprised of Sepharose 4B-L-tyrosine-p-aminobenzoic acid. The results showed that most of the compounds (3,4,5a,5d-h) inhibited and some of them (5c,5i-l) activated the tyrosinase enzyme activity. The molecular calculations were performed using Gaussian software for the synthesized compounds to explain the experimental results.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemistry*
  • Catechol Oxidase / antagonists & inhibitors*
  • Catechol Oxidase / metabolism
  • Chalcone / chemistry*
  • Dose-Response Relationship, Drug
  • Enzyme Activation / drug effects
  • Molecular Structure
  • Software*
  • Structure-Activity Relationship
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / pharmacology*

Substances

  • Carbazoles
  • carbazole
  • Chalcone
  • Urea
  • Catechol Oxidase