Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1224-1233.DOI: 10.6023/cjoc202009050 Previous Articles     Next Articles



赵雨珣1, 王芸芸1, 张成龙1, 徐徐1, 王石发1,*()   

  1. 1 南京林业大学林业资源高效加工利用协同创新中心 化学工程学院 南京 210037
  • 收稿日期:2020-09-24 修回日期:2020-10-22 发布日期:2020-12-01
  • 通讯作者: 王石发
  • 基金资助:

Synthesis of Novel Camphor Sulfamoxime Ether Derivatives and Its Application in Antitumor Activity

Yuxun Zhao1, Yunyun Wang1, Chenglong Zhang1, Xu Xu1, Shifa Wang1,*()   

  1. 1 Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering,Nanjing Forestry University, Nanjing 210037
  • Received:2020-09-24 Revised:2020-10-22 Published:2020-12-01
  • Contact: Shifa Wang
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    Natural National Science Foundation of China(32071707)

Based on the combination principle in drug design, a series of camphor sulfamoxime ether derivatives were designed and synthesized with (+)-10-camphorsulfonic acid as the staring materials via acyl chlorination, acyl amidation and condensation. The target compounds were characterized by 1H NMR, 13C NMR and HRMS spectra. In addition, the antiproliferative effects of compounds were evaluated on a panel of human adherent cell lines (A549, Hela, MCF-7 and LO2) by means of methyl thiazolyl tetrazolium (MTT) assays. Noticeably, (+)-1-(2-((benzyloxy)imino)-7,7-dimethylbicyclo[2.2.1]-heptan- 1-yl)-N-(3-(trifluoromethyl)phenyl)methanesulfonamide (4r) possessed excellent antiproliferative against A549 (6.75 μmol? L –1), Hela (7.93 μmol?L –1) and MCF-7 (4.51 μmol?L –1). Flow cytometry was used to detect cell cycle progression and apoptosis, and morphological change of apoptosis was observed by Hoechst 33258 staining. Levels of reactive oxygen specy (ROS) and mitochondrial membrane potential were measured by DCFH-DA and JC-1, respectively. These results indicated that compound 4r could cause cell cycle arrest at G0/G1 phase and triggered apoptosis in MCF-7 cells. Furthermore, 4r could induce the accumulation of ROS and mitochondrial disruption. Taken together, compound 4r could be a potential anticancer drug candidate.

Key words: camphor sulfamoxime ether, antitumor activity, G0/G1 phase arrest, apoptosis