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Synthesis of multiple boron-containing analogs via Ugi-4CR

Research on Chemical Intermediates volume 45, pages 103–118 (2019)Cite this article

Abstract

One of the most significant challenges in boron neutron capture therapy (BNCT) is to have an ideal boron delivery agent which can deliver sufficient numbers of boron atoms to designated tumor cells. In this work, mild synthetic conditions for synthesis of dipeptidyl multiple boron-containing analogs under microwave-assisted condition were investigated. The results showed that the reaction generally took place at 50 °C, but higher reaction temperature was required when a fluorinated building block was used. The resulting peptidyl skeletons generated by Ugi four-component reaction resemble basic cell metabolites and could potentially be used as alternative replacements for current boron carrier agents in BNCT.

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Acknowledgements

This research was supported by the Ministry of Science and Technology in Taiwan (MST-104-2113-M-032-011, MST-105-2113-M-032-002). We thank the Department of Chemistry of Tamkang University for equipment and financial support. We thank Ms. Shen–Shen Chen for conducting 11B NMR experiments.

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Authors and Affiliations

  1. Department of Oncology, Taipei Veterans General Hospital, Taipei City, Taiwan

    Yi-Wei Chen

  2. Department of Chemistry, Tamkang University, No. 151 Yingzhuan Rd., Tamsui Dist., New Taipei City, 25137, Taiwan

    Pei-Chun Liao, Yu-Xuan Zhang, Shang-Yi Yeh, Yu-Hsuan Wu, Shuo-Bei Qiu, Pei-Ni Tsai, Zhuo Xin, Yen-Yu Ting, Hsien-Chi Chen, Siu-Fung Cheung, Chen-Yun Hsu, Wan-Hsing Lien & Po-Shen Pan

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  1. Yi-Wei Chen
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Correspondence to Po-Shen Pan.

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Chen, YW., Liao, PC., Zhang, YX. et al. Synthesis of multiple boron-containing analogs via Ugi-4CR. Res Chem Intermed 45, 103–118 (2019). https://doi.org/10.1007/s11164-018-3629-0

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  • DOI: https://doi.org/10.1007/s11164-018-3629-0

Keywords

  • Boron neutron capture therapy
  • Boron
  • Multicomponent reaction
  • Ugi reaction