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

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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.

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Acknowledgments

This study was financially supported by the grants from The Scientific and Research Council of Turkey (Grant No: TBAG-2376) and Dumlupinar University Research Fund (Grant No: 52). The authors would like to thank Department of Chemistry, Faculty of Sciences, Atatürk University for providing spectroanalytical facilities and Department of Physics, Faculty of Arts and Sciences, Dumlupinar University for FT-IR measurements.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Dumlupinar University, 43100, Kutahya, Turkey

    Rahmi Kasımoğulları, Hamdiye Duran & Samet Mert

  2. Department of Chemistry, Faculty of Sciences, Cankiri Karatekin University, 18100, Cankiri, Turkey

    Ayşe Şahin Yağlıoğlu & İbrahim Demirtaş

Authors
  1. Rahmi Kasımoğulları
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  2. Hamdiye Duran
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  3. Ayşe Şahin Yağlıoğlu
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  4. Samet Mert
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Correspondence to Rahmi Kasımoğulları.

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Kasımoğulları, R., Duran, H., Yağlıoğlu, A.Ş. et al. Design, synthesis, characterization, and antiproliferative activity of novel pyrazole-3-carboxylic acid derivatives. Monatsh Chem 146, 1743–1749 (2015). https://doi.org/10.1007/s00706-015-1450-7

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  • DOI: https://doi.org/10.1007/s00706-015-1450-7

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