Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives

KURT B. Z., Sonmez F., Bilen C., Ergun A., Gencer N., Arslan O., ...Daha Fazla

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, cilt.31, sa.6, ss.991-998, 2016 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 31 Sayı: 6
  • Basım Tarihi: 2016
  • Doi Numarası: 10.3109/14756366.2015.1077823
  • Dergi Adı: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.991-998
  • Anahtar Kelimeler: ABTS, antioxidant, carbonic anhydrase, coumarin, CUPRAC, sulphonamide, SELECTIVE INHIBITORS, TERTIARY BENZENESULFONAMIDES, COUMARINS, POLYPHENOLS, TARGETS, POTENT, MODE
  • Yıldız Teknik Üniversitesi Adresli: Hayır

Özet

New secondary benzenesulphonamide-substituted coumarylthiazole derivatives were synthesized and their inhibitory effects on purified carbonic anhydrase I and II were evaluated using CO2 as a substrate. The result showed that all the synthesized compounds exhibited inhibitory activity on both hCA I and hCA II with N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl) naphthalene-2-sulphonamide (5f, IC50 value of 5.63 and 8.48 mu M, against hCA I and hCA II, respectively) as the strongest inhibitor revealed from this study. Structure-activity relationship revealed that the inhibitory activity of the synthesized compounds is related to the type of the halogen and bulky substituent on the phenyl ring. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were assayed. 4-methoxy-N-(4-(2-oxo-2H-chromen-3-yl) thiazol-2-yl) benzenesulphonamide (5e) exhibited the strongest ABTS and CUPRAC activity with IC50 value of 48.83 mu M and A(0.50) value of 23.29 mu M ,