Synthesis and antitumor activity evaluation of quinazoline derivatives bearing piperazine-1-carbodithioate moiety at C4-position

Bioorg Med Chem Lett. 2016 Oct 1;26(19):4666-4670. doi: 10.1016/j.bmcl.2016.08.060.

Ying Zhang ¹, Chao-Rui Yang ¹, Xue Tang ¹, Sheng-Li Cao ², Ting-Ting Ren ¹, Man Gao ¹, Ji Liao ³, Xingzhi Xu ⁴

Affiliations

1 Department of Chemistry, Capital Normal University, Beijing 100048, China.
2 Department of Chemistry, Capital Normal University, Beijing 100048, China. Electronic address: slcao@cnu.edu.cn.
3 School of Medicine, Shenzhen University, Shenzhen, Guangdong 518060, China; Beijing Key Laboratory of DNA Damage Response, College of Life Science, Capital Normal University, Beijing 100048, China.
4 School of Medicine, Shenzhen University, Shenzhen, Guangdong 518060, China; Beijing Key Laboratory of DNA Damage Response, College of Life Science, Capital Normal University, Beijing 100048, China. Electronic address: xingzhi.xu@szu.edu.cn.

PMID: 27575478 DOI: 10.1016/j.bmcl.2016.08.060

Abstract

A series of quinazoline derivatives bearing piperazine-1-carbodithioate moiety at the C4-position were synthesized using piperidine and 1-bromo-3-chloropropane as starting Materials via eight steps. Final compounds 8a-q and 9a-i were evaluated for their antiproliferative activity against human lung Cancer A549, breast adenocarcinoma MCF-7, and colorectal Cancer HCT-116 cell lines. The results showed that fourteen of twenty-six final compounds inhibited the proliferation of three Cancer cell lines with IC50 values less than 10μM. When treated with a representative compound 8n, HCT-116 cells were arrested at G0/G1 phase of the cell cycle. This provided a clue to further investigation of the mechanism of action.

Keywords

Antiproliferative activity; Cell cycle; Piperazine-1-carbodithioate; Quinazoline; Synthesis.

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