胡桃醌
化学
劳森
赫拉
细胞毒性
萘醌
1,4-萘醌
酰化
表皮样癌
体外
氧化还原
白花丹
立体化学
生物化学
药物化学
有机化学
催化作用
内科学
癌症
生物
医学
遗传学
作者
Chien‐Chang Shen,Shakil N. Afraj,Chia‐Cheng Hung,Balaji D. Barve,Li Jen Kuo,Lin Zhang,Hisu-O. Ho,Yao‐Haur Kuo
标识
DOI:10.1016/j.bmcl.2021.127976
摘要
A series of 1,4-naphthoquinone derivatives of lawsone (1), 6-hydroxy-1,4-naphthoquinone (2), and juglone (3) were synthesized by alkylation, acylation, and sulfonylation reactions. The yields of lawsone derivatives 1a-1k (type A), 6-hydroxy-1,4-naphthoquinone derivatives 2a-2j (type B), and juglone derivatives 3a-3h (type C) were 52–99%, 53–96%, and 28–95%, respectively. All compounds were tested in vitro for the cytotoxicity against human oral epidermoid carcinoma (KB) and cervix epithelioid carcinoma (HeLa) cells and their structure–activity relationship was studied. Compound 3c was found to be most potent in KB cell line (IC50 = 1.39 µM). Some compounds were evaluated for DNA topoisomerase I inhibition. Compounds 2c, 3, 3a, and 3d showed topoisomerase inhibition activity with IC50 values of 8.3–91 µM. Standard redox potentials (E°) of all naphthoquinones in phosphate buffer at pH 7.2 were examined by means of cyclic voltammetry. A definite correlation has been found between the redox potentials and inhibitory effects of type A compounds.
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