Synthesis and Cytotoxicity of N-Substituted Dibenzo[a,j]xanthene-3,11-dicarboxamide Derivatives

Yongbin Song; Yihui Yang; Lijun Wu; Naiwei Dong; Shang Gao; Hongrui Ji; Xia Du; Bo Liu; Guoyou Chen

doi:10.3390/molecules22040517

Synthesis and Cytotoxicity of N-Substituted Dibenzo[a,j]xanthene-3,11-dicarboxamide Derivatives

Molecules. 2017 Mar 23;22(4):517. doi: 10.3390/molecules22040517.

Authors

Yongbin Song¹, Yihui Yang², Lijun Wu³, Naiwei Dong⁴, Shang Gao⁵, Hongrui Ji⁶, Xia Du⁷, Bo Liu⁸, Guoyou Chen⁹

Affiliations

¹ School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China. [email protected].
² College of Pharmacy, Harbin Medical University, Harbin 150081, China. [email protected].
³ College of Pharmacy, Harbin Medical University, Harbin 150081, China. [email protected].
⁴ College of Pharmacy, Harbin Medical University, Harbin 150081, China. [email protected].
⁵ College of Pharmacy, Harbin Medical University, Harbin 150081, China. [email protected].
⁶ School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China. [email protected].
⁷ School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China. [email protected].
⁸ School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China. [email protected].
⁹ College of Pharmacy, Harbin Medical University Daqing Campus, Daqing 163319, China. [email protected].

Abstract

In order to study the structure-activity relationships of xanthene derivatives, four series of N-substituted 14-aryl-14H-dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives were synthesized. The structures of all compounds were identified by ¹H-NMR, HR-MS and IR spectra, in which compounds 6a-h were further identified by ¹³C-NMR spectra. The in vitro antitumor activity of the synthesized compounds was tested by MTT assay. Most of them displayed strong inhibitory activity on human hepatocellular carcinoma cell lines (SK-HEP-1, HepG2 and SMMC-7721 cells) and acute promyelocytic leukemia NB4 cells. Compounds 6c-6e exhibited significant inhibitory activity against NB4 cells with IC₅₀ values of 0.52 μM and 0.76 μM, respectively, much lower than 5.31 μM of the positive control As₂O₃.

Keywords: NMR spectroscopy; cytotoxicity; dibenzo[a,j]xanthenes; synthesis design.

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Drug Screening Assays, Antitumor
Hep G2 Cells
Humans
Molecular Structure
Xanthenes / chemical synthesis*
Xanthenes / chemistry
Xanthenes / pharmacology*

Substances

Antineoplastic Agents
Xanthenes