Synthesis and biological activities of artemisinin-piperazine-dithiocarbamate derivatives

Eur J Med Chem. 2019 May 1:169:21-28. doi: 10.1016/j.ejmech.2019.02.071.

Jia-Ying Yu ¹, Xue-Qiang Li ¹, Meng-Xue Wei ²

Affiliations

1 State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China.
2 State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China. Electronic address: weimengxue@nxu.edu.cn.

PMID: 30852384 DOI: 10.1016/j.ejmech.2019.02.071

Abstract

Twelve derivatives of artemisinin-piperazine-dithiocarbamate have been synthesised, and some of them showing good in vitro cytotoxic activity. Compound 3g exhibits the best inhibitory activity against SMMC-7721 cell lines with an IC₅₀ of 0.0025 ± 0.04 μM for 72 h, but the toxicity was lower against LO2 cell lines with an IC₅₀ of 0.18 ± 0.04 μM for 72 h. The results indicate that compound 3g is more cytotoxic towards Cancer cell lines than towards benign cell lines compared with vincristine in vitro. And compound 3g also has good inhibitory activity against colon, breast and prostate Cancer cells. Meanwhile, we have also proposed the six-member ring mechanism of DMSO in catalysing the esterification of hydroxyl and acyl chloride. Instead of using the hydroxyl, we can obtain the nucleophilic substitution production simply and efficiently without a Lewis acid, which has not been reported previously.

Keywords

Biological activities; Cancer; Dithiocarbamate; Reaction mechanism; Synthesis.

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