- Synthesis and cytotoxicity of n-substituted dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives
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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.
- Song, Yongbin,Yang, Yihui,Wu, Lijun,Dong, Naiwei,Gao, Shang,Ji, Hongrui,Du, Xia,Liu, Bo,Chen, Guoyou,Dembinski, Roman
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- Design, synthesis and anticancer activity of N3,N 11-bis(2-hydroxyethyl)-14-aryl-14H-dibenzo[a,j]xanthenes-3, 11-dicarboxamide
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A series of novel N3,N11-bis(2-hydroxyethyl)-14-aryl- 14H-dibenzo[a,j]xanthenes-3,11-dicarboxamide, three N3,N 11-bis(2-hydroxyethyl)-14-aryl-14H-dibenzo[a,j]xanthene-3, 11-dimethanamine derivatives and their intermediates 14-aryl-14H-dibenzo[a,j] xanthenes-3,11-dicarboxylic acid, were synthesized, and the structures of which were characterized by 1H-NMR, 13C-NMR, high resolution (HR)-MS, and IR spectra. The antitumor activities of these molecules were evaluated on five cancer cell lines. The results of in vitro assay against human hepatocellular carcinoma cell lines (SK-HEP-1 and HepG2 and SMMC-7721 cells), acute promyelocytic leukemia NB4 cells and uterine cervix cancer HeLa cells, show several compounds to be endowed with cytotoxicity in micromolar to submicromolar range. The carboxamide derivatives 6c and 6e exhibitted good inhibition on NB4 cancer cells, and the IC50 values of which were 0.82 μm and 0.96 μm, respectively, much lower than 5.01 μm of the positive control As2O3. Flow cytometric analysis results revealed that compounds 6e and 6f may induce tumor cell apoptosis.
- Song, Yongbin,Yang, Yihui,You, Jun,Liu, Bo,Wu, Lijun,Hou, Yunlong,Wang, Wenji,Zhu, Jiuxin
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p. 167 - 175
(2013/03/28)
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