Synthesis and paroxonase activities of novel bromophenols


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Akbaba Y., Turkes C., Polat L., SÖYÜT H. , ŞAHİN E., MENZEK A., ...More

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.28, no.5, pp.1073-1079, 2013 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 5
  • Publication Date: 2013
  • Doi Number: 10.3109/14756366.2012.715287
  • Title of Journal : JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Page Numbers: pp.1073-1079
  • Keywords: Bromination, bromophenols, natural products, demethylation, paroxonase activity, IN-VITRO, CARBONIC-ANHYDRASE, PARAOXONASE, ANESTHETICS, PON1

Abstract

Three novel bromophenols 10-12 were synthesized. Acylation of veratrole (4) with 2,3-dimethoxy benzoic acid (5) gave a kown diarylmethanone 6. Bromination of 6 with different equivalents of molecular bromine afforded new di and tribrominated compounds 7-9 which were converted to their corresponding bromophenols 10-12 via O-demethylation with BBr3. Paraoxonase-1 (PON1) was purified from human serum with approximately 42% and 3584 U x mg(-1) specific activity. The synthesized compounds 6-12 showed inhibitory effects on paraoxonase-1 (PON1) which is an organophosphate (OP) hydrolyser and an antioxidant bioscavenger enzyme. IC50 values were determined in the range of 0.123-1.212 mM.