Novel pyrazole-3,4-dicarboxamides bearing biologically active sulfonamide moiety as potential carbonic anhydrase inhibitors
ARABIAN JOURNAL OF CHEMISTRY, cilt.12, sa.8, ss.2740-2748, 2019 (SCI-Expanded, Scopus)
- 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/).