Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects

GÜL H. İ., Kucukoglu K., Yamali C., BİLGİNER S., YUCA H., Ozturk I., ...Daha Fazla

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, cilt.31, sa.4, ss.568-573, 2016 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 31 Sayı: 4
  • Basım Tarihi: 2016
  • Doi Numarası: 10.3109/14756366.2015.1047359
  • Dergi Adı: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.568-573
  • Anahtar Kelimeler: 2-Acethylfuran, 2-acethylthiophene, acetophenones, carbonic anhydrase, enzyme inhibition, indanone, sulfonamide, TROUT ONCORHYNCHUS-MYKISS, ERYTHROCYTES IN-VITRO, THERAPEUTIC APPLICATIONS, SULFONAMIDE DERIVATIVES, ENZYME-ACTIVITY, ISOENZYMES I, ISOZYMES I, ISOFORMS I, PURIFICATION, PEROXIDASE
  • Çukurova Üniversitesi Adresli: Hayır

Özet

In this study, 4-(2-substituted hydrazinyl)benzenesulfonamides were synthesized by microwave irradiation and their chemical structures were confirmed by H-1 NMR, (CNMR)-C-13, and HRMS. Ketones used were: Acetophenone (S1), 4-methylacetophenone (S2), 4-chloroacetophenone (S3), 4-fluoroacetophenone (S4), 4-bromoacetophenone (S5), 4-methoxyacetophenone (S6), 4-nitroacetophenone (S7), 2-acetylthiophene (S8), 2-acetylfuran (S9), 1-indanone (S10), 2-indanone (S11). The compounds S9, S10 and S11 were reported for the first time, while S1-S8 was synthesized by different method than literature reported using microwave irradiation method instead of conventional heating in this study. The inhibitory effects of 4-(2-substituted hydrazinyl) benzenesulfonamide derivatives (S1-S11) against hCA I and II were studied. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized sulphonamide derivatives with K-is in the range of 1.79 +/- 0.22-2.73 +/- 0.08 nM against hCA I and in the range of 1.72 +/- 0.58-11.64 +/- 5.21nM against hCA II, respectively.