Journal of Chinese Pharmaceutical Sciences ›› 2018, Vol. 27 ›› Issue (3): 159-169.DOI: 10.5246/jcps.2018.03.017

• Original articles • Previous Articles     Next Articles

Design, synthesis and antitumor activity evaluation of novel 2,6-dichloro-3,5-dinitrotoluene derivatives

Jiayuan Jiao1, Hao Hu2, Siyuan Wei1, Wanqiu Wang1, He Lin3, Baoshan Chai1*   

  1. 1. Pharmaceutical Research Laboratory, Shenyang Research Institute of Chemical Industry Co., Ltd., Shenyang 110021, China
    2. Shenyang Pharmaceutical University, Shenyang, 110016, China
    3. Safety Evaluation Center, Shenyang Research Institute of Chemical Industry Co., Ltd, Shenyang 110021, China
  • Received:2017-12-19 Revised:2018-01-09 Online:2018-03-31 Published:2018-03-13
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  • Supported by:
    The Natural Science Foundation of Liaoning province (Grant No. 20170540730).


A series of novel 2,6-dichloro-3,5-dinitrotoluene derivatives were designed, synthesized in the present study, and their antitumor activities against five cell lines (A431, HepG2, A549, HT-29 and HEK-293) were tested. Most of the compounds exhibited moderate-to-significant cytotoxicity and high selectivity against one or more cell lines in comparison with cisplatin. Studies on their preliminary structure-activity relationships (SARs) indicated that compounds containing phenyl (piperazin-1-yl) methanone groups, especially chlorine atom at 4-position of the phenyl ring, were more effective. Compound 4g was found to be the most potent derivative with IC50 values of 1.04, 3.20, 6.93, 4.10 and 20.15 μmol/L against A431, Hep G2, A549, HT-29 and HEK-293 cell lines, respectively, which was better than positive control cisplatin, one of the most clinically used chemotherapeutic drugs.

Key words: 2,6-Dichloro-3,5-dinitrotoluene, Cytotoxic activity, Structure-activity relationships

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