Design, synthesis of novel C-3′-N-sulfonyl modified taxane analogues from 1-deoxybaccatin VI and their impact on anti-HCC activity

Abstract

A new series of C-3′-N-sulfonyl paclitaxel analogs were designed and synthesized from 1-deoxybaccatin VI and their structures were confirmed by ¹H NMR, ¹³C NMR and high resolution MS. The synthesized compounds were evaluated for their in vitro anti-Hepatocellular carcinoma (HCC) activity against human hepatoma (HepG2) cell line. Bioassay results showed that compounds 17c, 17d and 17f exhibited more potent inhibitory activity against HepG2 cell line in comparison with paclitaxel. It is suggested that paclitaxel analogs containing the C-3′-N-sulfonyl could be considered as a precursor structure for further synthesis of more potent analogues.

Graphical Abstract

Keywords:

• Paclitaxel
• 1-deoxybaccatin VI
• synthesis
• anti-HCC activity
• 3′-N-sulfonyl

Acknowledgements

The authors are grateful to Prof. Junjie Xiao, School of Life Sciences Shanghai University, for their help in the activity assay. The authors also thank Dr. H. Deng, the Instrumental Analysis & Research Center of Shanghai University, for structural analysis.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by the the National Natural Science Foundation of China [grant numbers 21272154 & 81202402].