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Synthesis and anticancer activities of 1,4-phenylene-bis-N-acetyl- and N-phenylpyrazoline derivatives

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Abstract

Novel 1,4-phenylene-bis-N-acetyl- (3a–h) and bis-N-phenylpyrazoline derivatives (4a–h) were obtained by addition of hydrazine hydrate and phenylhydrazine to bis-chalcone derivatives (1a–h) in acetic acid and acetic acid/ethanol for 4 and 8 h in reflux conditions, respectively. The structures of the obtained bis-N-acetylpyrazoline and bis-N-phenylpyrazoline derivatives were characterized by nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic methods and elemental analysis. Compounds 3a–h and 4a–h were investigated to evaluate their anticancer activities against C6 (rat brain tumor cells) and HeLa (human uterus carcinoma) in vitro using a dose-dependent assay from 5 to 100 μM with 5-fluorouracil (5-FU) as standard anticancer drug. Compound 3a showed higher cell-selective activity compared with 5-FU against HeLa cells. Compounds 3a–h (except 3d) were shown to have better activities than 5-FU against both cells, particularly at high concentration. Compound 4c showed higher cell-selective activity compared with 5-FU against C6 cells. Compound 3a may be particularly promising as an anticancer drug against HeLa cells.

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Acknowledgments

The authors are indebted to the Gaziosmanpasa University Scientific Research Projects Commission (Project No. BAP2011/95) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250, Tokat, Turkey

    Meliha Burcu Gürdere, Onur Gümüş, Yakup Budak & Mustafa Ceylan

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

    Ayse Sahin Yaglioglu

Authors
  1. Meliha Burcu Gürdere
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  2. Onur Gümüş
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  3. Ayse Sahin Yaglioglu
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  4. Yakup Budak
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  5. Mustafa Ceylan
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Corresponding author

Correspondence to Meliha Burcu Gürdere.

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Gürdere, M.B., Gümüş, O., Yaglioglu, A.S. et al. Synthesis and anticancer activities of 1,4-phenylene-bis-N-acetyl- and N-phenylpyrazoline derivatives. Res Chem Intermed 43, 1277–1289 (2017). https://doi.org/10.1007/s11164-016-2697-2

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