Journal
RSC ADVANCES
Volume 10, Issue 48, Pages 28644-28652Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ra06043g
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Funding
- China Scholarship Council [201706660015]
- Guangxi Scholarship Fund of Guangxi Education Department [guijiaoshipei-2016-22]
- Promotion of Young and Middle-aged Teachers' Basic Scientific Research Ability in Guangxi Universities by Guangxi Education Department [2019KY0329]
- Opening Project of First-class Discipline Construction in Guangxi [2019XK047, 2019XK132]
- Guangxi Key Laboratory of Zhuang and Yao Ethnic Medicine [GXZYZZ2019-7, GXZYKF2019-6, guikejizi-2014-32]
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Using flavonoids and dichlone as substrates, benzonaphthofuroquinones (1,2,3,5,6, novel;4new) and benzoylnaphthindolizinediones (7,8, known;9, new) were synthesized through common base-catalyzed method and a new method of combining base-catalyzed with O-2/H2O exposing. The possible reaction mechanisms may involve the process like isomerization, hydration, oxidation, decomposition and intermolecular condensation. Benzonaphthofuroquinones (2,3,4,5) were found to exhibit potent cytotoxicity against carcinoma cell lines and low toxicity to normal cell lines. The compounds4and5not only expressed a significant late-stage-apoptosis against human leukemia and melanoma, but also promoted the cleavage of caspase-3 and PARP in human leukemia, which suggested that the late-stage-apoptosis and caspase-3 pathway may be responsible for the cytotoxicities of these benzonaphthofuroquinones. The replacement of the furan ring with pyrrole system in benzoylnaphthindolizinediones (7,8,9) resulted in the loss of anticancer activity.
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