Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur

Journal of the Brazilian Chemical Society

Cerri, Murilo F.¹  Daltoé, Renata D.¹  Lacerda Júnior, Valdemar¹  Romão, Wanderson¹  Universidade Federal do Espírito Santo, Vitória, BR¹  Madeira, Klesia P.¹  Universidade Federal de São João Del-Rei, Divinópolis, BR¹  Delarmelina, Maicon¹  Taranto, Alex G.¹  Greco, Sandro J.¹  Rangel, Leticia B. A.¹ 

关键词:  1;    4-naphthoquinone;    antineoplastic activity;    topoisomerase;    PI3K;    nucleophilic substitution;   

DOI  :  10.5935/0103-5053.20150157

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Eleven 2,3-(substituted)-1,4-naphthoquinone derivatives were synthesized in yields ranging from 52-89%. These derivatives were evaluated for their cytotoxic effects on human lungs (H460), triple-negative breast (MDA-MB-231) and ovarian (A2780) cancer cell lines. Compounds 5f and 8 showed IC50values of 3.048 × 10-5 mol L-1 and 4.24 × 10-6 mol L-1 for H460; 5c and 8showed IC50 values of 2.16 × 10-5 mol L-1 and 1.60 × 10-5 mol L-1 for MDA-MB-231, and 5gand 8 showed IC50 values of 2.68 × 10-6 mol L-1 and 3.89 × 10-6 mol L-1 for A2780. Additionally, we conducted a docking study with the four most active compounds and the therapeutic targets PI3K and topoisomerase II showing the pharmacophoric conformation of these compounds.

【 授权许可】

Unknown