Novel pyrazole-3,4-dicarboxamides bearing biologically active sulfonamide moiety as potential carbonic anhydrase inhibitors

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Mert S., Alım Z., İşgör M. M., Anıl B., Kasımoğulları R., Beyde S.

ARABIAN JOURNAL OF CHEMISTRY, cilt.12, sa.8, ss.2740-2748, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 12 Sayı: 8
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.arabjc.2015.05.020
  • Dergi Adı: ARABIAN JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2740-2748
  • Anahtar Kelimeler: Pyrazole, Pyrazole-3,4-dicarboxamide, Synthesis, Reduction, Carbonic anhydrase, Enzyme inhibition, X-RAY CRYSTALLOGRAPHY, SELECTIVE INHIBITOR, ISOZYMES IX, ISOFORMS I, DERIVATIVES, XII, ANTIBACTERIAL, SILDENAFIL, ANALOGS, SERIES
  • Atatürk Üniversitesi Adresli: Evet

Özet

In this study a series of pyrazole-3,4-dicarboxamide (3-10) derivatives bearing sulfonamide moiety were synthesized starting from 1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3,4-dicarboxylic acid (1). The structures of synthesized molecules were characterized by FT-IR, H-1 NMR, C-13 NMR, and elemental analysis methods. Human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified separately from erythrocyte cells by the Sepharose-4B-L-tyrosine-sulfa nilamide affinity column chromatography and inhibitory effects of newly synthesized sulfonamides on esterase activities of these isoenzymes have been studied as in vitro. The K-i values of compounds were found in the range of 0.056-110.400 mu M for hCA I and 0.057-533.400 mu M for hCA II. Compound 4 has the highest inhibitory effect for hCA I and hCA II while compound 5 showed lowest inhibition. The structure-activity relationships for the inhibition of these isoforms with the pyrazole-sulfonamides reported here were also elucidated. (C) 2015 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).