Synthesis and paroxonase activities of novel bromophenols

AKBABA Y., TURKES C., POLAT L., SOYUT H., ŞAHİN E., MENZEK A., ...Daha Fazla

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, cilt.28, sa.5, ss.1073-1079, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 28 Sayı: 5
  • Basım Tarihi: 2013
  • Doi Numarası: 10.3109/14756366.2012.715287
  • Dergi Adı: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1073-1079
  • Anahtar Kelimeler: Bromination, bromophenols, natural products, demethylation, paroxonase activity, IN-VITRO, CARBONIC-ANHYDRASE, PARAOXONASE, ANESTHETICS, PON1
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.