Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects

Bulbul, Metin; Kasimogullari, Rahmi; Küfrevioğlu, Ömer İrfan

doi:10.1080/14756360701626173

Makale Tam Makale Uluslararası 2008

Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects

Metin Bulbul, Rahmi Kasimogullari, Ömer İrfan Küfrevioğlu

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY Cilt 23 · Sayı 6 · ss. 895–900 · 01.01.2008

DOI ile aç

Özet

Pyrazole carboxylic acid amides of 5-amino-1,3,4-thiadiazole-2-sulfonamide were synthesized from 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carbonyl chloride and 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride. Carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from human erythrocyte cells by the affinity chromatography method. The inhibitory effects of 5-amino-1,3,4-thiadiazole-2-sulfonamide 1, acetazolamide 2 and new synthesized amides on these isozymes have been studied in vitro. The I50 concentrations (the concentration of inhibitor producing a 50% inhibition of CA activity) against hydratase activity ranged from 1.2 to 2.2nM for hCA-I and from 0.4 to 2nM for hCA-II. The I50 values against esterase activity ranged from 1.4 to 8nM for hCA-I and from 1.3 to 6nM for hCA-II. The Ki values were observed between 8.210-5 to 6.210-4 M for hCA-I and between 2.910-4 to 8.210-4 M for hCA-II. The comparison of new synthesized amides to 5-amino-1,3,4-thiadiazole-2-sulfonamide 1, acetazolamide 2 indicated that the new synthesized compounds (18-23) inhibit CA activity more potently than the parent compounds.

Anahtar kelimeler

DESIGN AGENTS carbonic anhydrase INHIBITION IN-VIVO SULFONAMIDES IX CYCLIC OXALYL COMPOUNDS pyrazole carboxylic acids hydratase activity esterase activity ISOZYME-XII ISOFORM-II IV

Atıf için künye

Bulbul, M., Kasimogullari, R., & Küfrevioğlu, Ö. İ. (2008). Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 23(6), 895–900. https://doi.org/10.1080/14756360701626173

BibTeX

@article{bulbul2008-68709,
  author = {Bulbul, Metin and Kasimogullari, Rahmi and Küfrevioğlu, Ömer İrfan},
  title = {Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects},
  journal = {JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY},
  year = {2008},
  volume = {23},
  number = {6},
  pages = {895--900},
  issn = {1475-6366},
  doi = {10.1080/14756360701626173},
  url = {https://akademik.atauni.edu.tr/yayinlar/68709-amide-derivatives-with-pyrazole-carboxylic-acids-of-5-amino-134-thiadiazole-2}
}