Chinese Journal of Organic Chemistry >
Synthesis of Novel Camphor Sulfamoxime Ether Derivatives and Its Application in Antitumor Activity
Received date: 2020-09-24
Revised date: 2020-10-22
Online published: 2020-12-01
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.
Yuxun Zhao , Yunyun Wang , Chenglong Zhang , Xu Xu , Shifa Wang . Synthesis of Novel Camphor Sulfamoxime Ether Derivatives and Its Application in Antitumor Activity[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1224 -1233 . DOI: 10.6023/cjoc202009050
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