State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China.
State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China.
Eur J Med Chem. 2019 May 1;169:21-28. doi: 10.1016/j.ejmech.2019.02.071. Epub 2019 Mar 2.
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 IC of 0.0025 ± 0.04 μM for 72 h, but the toxicity was lower against LO2 cell lines with an IC 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.
已合成了 12 种青蒿素-哌嗪-二硫代氨基甲酸酯衍生物，其中一些具有良好的体外细胞毒性。化合物 3g 对 SMMC-7721 细胞系的抑制活性最好，在 72 h 时的 IC 为 0.0025 ± 0.04 μM，但对 LO2 细胞系的毒性较低，在 72 h 时的 IC 为 0.18 ± 0.04 μM。结果表明，与长春新碱相比，化合物 3g 在体外对癌细胞系的细胞毒性大于对良性细胞系的细胞毒性。并且化合物 3g 对结肠、乳腺和前列腺癌细胞也具有良好的抑制活性。同时，我们还提出了 DMSO 在催化羟基和酰氯酯化反应中的六元环机制。我们可以不使用羟基，简单高效地获得亲核取代产物，而无需路易斯酸，这是以前没有报道过的。
