New NH-substituted 1,4-naphtho- and 1,4-benzo- quinones: Synthesis, characterization and potential antiproliferative effect against MDA-MB-231 cells

Abstract

Eleven new alkyl and aryl amino quinones were synthesized from quinones (2,3-dibromo-1,4-naphthoquinone 1, 2-bromo-1,4-naphthoquinone 2, p-benzoquinone 3 or 2,6-dichloro-1,4-benzoquinone 8) with primary amines. The structures of all compounds were characterized by spectroscopic technics and elemental analysis. The structure of 2-((6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)methylamino)-3-bromonaphthalene-1,4-dione (5a) was established by single crystal diffraction. 2-(2-(Ethylthio)ethylamino)naphthalene-1,4-dione (6b) was found to have noteworthy antiproliferative effect against MDA-MB-231 cells.

Graphical Abstract

Keywords:

• 1,4-Naphthoquinone
• p-Benzoquinone
• X-Ray structure determination
• MDA-MB-231 cells

Acknowledgments

This work was supported by Research Fund of the Istanbul University, Istanbul, Turkey. (Project Number: FBA-2017-22046). I am grateful to the Research Fund of Istanbul University, for financial support.