Synthesis and anticancer evaluation of novel 1,4-naphthoquinone derivatives containing a phenylamino-sulfanyl moiety.

Synthesis and anticancer evaluation of novel 1,4-naphthoquinone derivatives containing a phenylamino-sulfanyl moiety.

ChemMedChem. 2019 Jan 02;:

Authors: Yoo DJ, Ravichandiran P, Subramaniyan SA, Kim SY, Kim JS, Park BH, Shim KS

Abstract
1,4-Naphthoquinones are exceptional building blocks in organic synthesis and have been used to synthesize several well-known pharmaceutically active agents. Here we report the synthesis, structure characterization and biological evaluation of new sulfanyl-phenylamino-1,4-naphthoquinone derivatives (3-5aa). We evaluated the cytotoxic activity of the synthesized compounds against three human cancer cell lines, A549, HeLa and MCF-7. Most of the synthesized compounds displayed potent cytotoxic activity. Specifically, compounds 5e, 5f and 5p showed remarkable cytotoxic activity (IC50 in MCF-7 cells = 0.05 µM; 0.09 µM; 0.02 µM, respectively). The synthesized compounds showed low toxicity in HEK293 normal human kidney cells. We also examined the effects of compounds 5e, 5f and 5p on cell apoptosis analysis and cell cycle arrest in MCF-7 cells. The results confirmed that compounds 5e, 5f and 5p induced apoptosis and arrested the cell cycle at the G1 phase in MCF-7 cells. In addition, compounds 5e, 5f and 5p induced apoptosis through the upregulation of caspase-3 and caspase-7 protein and gene expression levels. Our findings demonstrate that compounds 5e, 5f and 5p could be potent anticancer agents against a number of cancers.

PMID: 30600915 [PubMed - as supplied by publisher]

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