Design, synthesis, characterization, and antiproliferative activity of novel pyrazole-3-carboxylic acid derivatives

Kasimoʇullari R., Duran H., Yaʇlioʇlu A. Ş., Mert S., Demirtaş İ.

Monatshefte fur Chemie, vol.146, no.10, pp.1743-1749, 2015 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 146 Issue: 10
  • Publication Date: 2015
  • Doi Number: 10.1007/s00706-015-1450-7
  • Journal Name: Monatshefte fur Chemie
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1743-1749
  • Keywords: Antiproliferative activity, Carboxylic acids, Heterocycles, NMR spectroscopy, Pyrazole, Vero cells
  • Ondokuz Mayıs University Affiliated: No

Abstract

In this study several novel 4-substituted-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid derivatives were synthesized. The structures of these pyrazole-3-carboxylic acid derivatives were characterized by FT-IR, 1H NMR, 13C NMR, and elemental analysis methods. Synthesized molecules were screened to evaluate their antiproliferative activities against Vero (African green monkey kidney), C6 (rat brain tumor), and HeLa (human uterus carcinoma) cells as in vitro. The tests were carried out as dose-dependent assay starting from 100 to 500 μg/cm3. Ethyl 1-(3-nitrophenyl)-5-phenyl-3-(phenylcarbamoyl)-1H-pyrazole-4-carboxylate exhibited the highest performance against HeLa, Vero, and C6 cells among the synthesized derivatives. Also, it showed better antiproliferative activity compared with 5-fluorouracil (5-FU) against Vero cell. Two compounds showed moderate antiproliferative activities against C6 cell line when compared with 5-FU. Also moderate antiproliferative activities against Vero and HeLa cell lines were found. Graphical abstract: (Chemical Equation Presented).