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Chemoselective synthesis, antiproliferative activities, and SAR study of 1H-pyrazol-5-yl-N,N-dimethylformamidines and pyrazolyl-2-azadienes

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Abstract

Chemoselective microwave-assisted amidination was successfully developed to synthesize 1H-pyrazol-5-yl-N,N-dimethylformamidines and pyrazolyl-2-azadienes. All of the starting materials and resulting products were tested against NCI-H226, NPC-TW01, and Jurkat cancer cells to evaluate their antiproliferative activities. 1H-Pyrazol-5-yl-N,N-dimethylformamidines 2b, 2c, and 2d were most potent with IC50 values in low micromolar range. The formyl group at C-4 position and the grafted amidinyl group in the main core of pyrazolic molecule were necessary for the inhibitory activity.

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Acknowledgments

We are grateful to the China Medical University (CMU100-S-TS-13) and the National Science Council of Republic of China for financial support (NSC 99-2320-B-039-014-MY3).

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Authors and Affiliations

  1. Graduate Institute of Pharmaceutical Chemistry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan, ROC

    Kau-Shan Wen, Yu-Ying Huang, Shin-Hun Juang & Fung Fuh Wong

  2. School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan, ROC

    Hui-Yi Lin

  3. Department of Medico Pharmaceutical Science, Nihon Pharmaceutical University, 10281, Komuro, Inamachi, Kita-Adachigun, Saitama, Japan

    Kimiyoshi Kaneko, Hiroyuki Takayama & Masayuki Kimura

Authors
  1. Kau-Shan Wen
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  2. Hui-Yi Lin
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  3. Yu-Ying Huang
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  4. Kimiyoshi Kaneko
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  5. Hiroyuki Takayama
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  6. Masayuki Kimura
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  7. Shin-Hun Juang
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  8. Fung Fuh Wong
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Corresponding authors

Correspondence to Shin-Hun Juang or Fung Fuh Wong.

Additional information

Kau-Shan Wen and Hui-Yi Lin have contributed equally to this work.

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Wen, KS., Lin, HY., Huang, YY. et al. Chemoselective synthesis, antiproliferative activities, and SAR study of 1H-pyrazol-5-yl-N,N-dimethylformamidines and pyrazolyl-2-azadienes. Med Chem Res 21, 3920–3928 (2012). https://doi.org/10.1007/s00044-011-9872-1

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  • DOI: https://doi.org/10.1007/s00044-011-9872-1

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