Design, synthesis and biological evaluation of novel pyrazole derivatives bearing sulfonamide scaffold as antiproliferative agents

Vurucu B., Mert S., Koldaş S., Demirtaş İ., Kasımoğulları R.

Journal of the Iranian Chemical Society, vol.20, no.5, pp.1107-1118, 2023 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 5
  • Publication Date: 2023
  • Doi Number: 10.1007/s13738-022-02738-x
  • Journal Name: Journal of the Iranian Chemical Society
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Page Numbers: pp.1107-1118
  • Keywords: Antiproliferative agents, Bioorganic chemistry, Heterocycles, Pyrazole carboxylic acids, Sulfonamides
  • Ondokuz Mayıs University Affiliated: No

Abstract

A series of novel N-methyl-substituted pyrazole carboxamide (10–17) and dicarboxamide derivatives (18–21) were efficiently obtained by the reaction of pyrazole-3-carboxylic acids (4,5) and pyrazole-3,4-dicarboxylic acid (8) with several aromatic and heteroaromatic sulfonamides. Synthesized sulfonamide derivatives were characterized using 1H NMR, 13C NMR, FT-IR, mass spectroscopy techniques. Antiproliferative activities of synthesized molecules were evaluated against the human cervical cancer cell line (HeLa) using the xCELLigence system (Real-Time Analyzer). According to the antiproliferative activity results, compound 16 showed the highest activity among the synthesized compounds with 64.10%, while starting compound 4 showed the highest at all with 80.82%. Graphical abstract: The methyl substituted pyrazole carboxylic (4) and carboxamide (16) derivatives with antiproliferative activities with 80.82% and 64.10%, respectively, and compound 13 with moderate activity (61.26%) against the human cervical cancer cell line could be a potential lead compounds for developing novel anticancer agents. [Figure not available: see fulltext.]