Journal of Enzyme Inhibition and Medicinal Chemistry (Jan 2020)

Design, synthesis and anticancer activity of naphthoquinone derivatives

  • Xiao-bao Shen,
  • Yang Wang,
  • Xuan-zhen Han,
  • Liang-quan Sheng,
  • Fu-fang Wu,
  • Xinhua Liu

DOI
https://doi.org/10.1080/14756366.2020.1740693
Journal volume & issue
Vol. 35, no. 1
pp. 773 – 785

Abstract

Read online

Basis on molecular docking and pharmacophore analysis of naphthoquinone moiety, a total of 23 compounds were designed and synthesised. With the help of reverse targets searching, anti-cancer activity was preliminarily evaluated, most of them are effective against some tumour cells, especially compound 12: 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl-4-oxo-4-((4-phenoxyphenyl)amino) butanoate whose IC50 against SGC-7901 was 4.1 ± 2.6 μM. Meanwhile the anticancer mechanism of compound 12 had been investigated by AnnexinV/PI staining, immunofluorescence, Western blot assay and molecular docking. The results indicated that this compound might induce cell apoptosis and cell autophagy through regulating the PI3K signal pathway.

Keywords