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Synthesis and evaluation of analgesic, anti-inflammatory, and anticancer activities of new pyrazole-3(5)-carboxylic acid derivatives

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Abstract

In this article, we synthesized a series of novel 1-benzyl-5(3)-p-tolyl-1H-pyrazole-3(5)-carboxylic acid derivatives and characterized by IR, 1H NMR, and mass spectroscopy. Compounds were evaluated for their in vivo analgesic and anti-inflammatory activity using the p-benzoquinone-induced writhing test and the carrageenan-induced paw edema model, respectively. Out of 14 compounds tested, 7a, 7c, 7e, 7f, 7i, 8a–b, and 8f–g exhibited potent analgesic and/or anti-inflammatory activity as compared to reference drugs aspirin and indomethacin. Anticancer activity of these compounds was assessed against five cancer cell lines with the MTT assay (HL-60, human promyelocytic leukemia cells; HeLa, human cervical cancer cells; Raji, human B lymphocyte cell line; MCF7, human breast adenocarcinoma cell line; MDA-MB-231, estrogen-independent human breast cancer cell line). Compounds 7a, 8a, and 8b with high anti-inflammatory activity, and also 7d and 7j with mild anti-inflammatory activity exhibited promising anticancer activity against some selected cell lines.

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Acknowledgments

This investigation was supported by a Scientific Research Grant 02/2010-20 awarded by Gazi University BAP. The authors greatly acknowledge D. A. Alkan (Department of Pharmacology) for her assistance for performing in vivo biological experiments. The authors report no conflicts of interest.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Etiler, 06330, Yenimahalle, Ankara, Turkey

    Burcu Çalışkan & Erden Banoglu

  2. Department of Medical Biology and Genetics, Faculty of Medicine, Gazi University, Etiler, 06100, Besevler, Ankara, Turkey

    Akın Yılmaz & Sevda Menevşe

  3. Department of Pharmacology, Faculty of Pharmacy, Gazi University, Etiler, 06330, Yenimahalle, Ankara, Turkey

    İlker Evren & Orhan Uludag

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  1. Burcu Çalışkan
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  2. Akın Yılmaz
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  3. İlker Evren
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  4. Sevda Menevşe
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  5. Orhan Uludag
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  6. Erden Banoglu
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Correspondence to Erden Banoglu.

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Çalışkan, B., Yılmaz, A., Evren, İ. et al. Synthesis and evaluation of analgesic, anti-inflammatory, and anticancer activities of new pyrazole-3(5)-carboxylic acid derivatives. Med Chem Res 22, 782–793 (2013). https://doi.org/10.1007/s00044-012-0072-4

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  • DOI: https://doi.org/10.1007/s00044-012-0072-4

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