Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

BİLGİNER S., GÜL H. İ., Erdal F. S., Sakagami H., LEVENT S., GÜLÇİN İ., ...More

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.34, no.1, pp.1722-1729, 2019 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 1
  • Publication Date: 2019
  • Doi Number: 10.1080/14756366.2019.1670657
  • Journal Name: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.1722-1729
  • Keywords: Anticancer, benzoxazolone, carbonic anhydrase, chalcone, cytotoxic, MANNICH-BASES, ANTICANCER, DERIVATIVES, CHALCONES, APOPTOSIS, ACETYLCHOLINESTERASE, BIOACTIVITIES, LICORICE, ACID
  • Anadolu University Affiliated: Yes

Abstract

In this study, new chalcone compounds having the chemical structure of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones (1?8) were synthesised and were characterised by H-1-NMR, C-13?-NMR, and HRMS spectra. Cytotoxic and carbonic anhydrase (CA) inhibitory effects of the compounds were investigated. Cytotoxicity results pointed out that compound 4, 6-[3-(4-trifluoromethylphenyl)-2-propenoyl]-3H-benzoxazol-2-one, showed the highest cytotoxicity (CC50) and potency-selectivity expression (PSE) value, and thus can be considered as a lead compound of this study. According to the CA inhibitory results, IC50 values of the compounds 1?8 towards hCA I were in the range of 29.74?69.57??M, while they were in the range of 18.14 ? 48.46??M towards hCA II isoenzyme. K-i values of the compounds 1?8 towards hCA I were in the range of 28.37???6.63?70.58???6.67??M towards hCA I isoenzyme and they were in the range of 10.85???2.14 ? 37.96???2.36??M towards hCA II isoenzyme.