Synthesis and paroxonase activities of novel bromophenols

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 × 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.

Graphical abstract

Keywords::

• Bromination
• bromophenols
• natural products
• demethylation
• paroxonase activity

Acknowledgment

Authors are indebted to the Department of Chemistry (Atatürk University) for research conditions.

Declaration of interest

This research was financed by grants from TÜBİTAK (The Scientific and Technological Research Council of Turkey) (Project no: TBAG-107T348).