Preparation and biological evaluation of novel acylhydrazide derivatives of 2,3-dichloronaphthoquinone

 Jomana Elaridi, Nour Bou Karroum, Kamal Bouhadir, Maamoun Fatfat and Hala Gali-Muhtasib

Department of Natural Sciences, School of Arts and Sciences, Lebanese American University, Beirut, 1102-2801, Lebanon

Department of Chemistry, Faculty of Arts and Sciences, American University of Beirut, Beirut, 11-0236, Lebanon

Department of Biology, and Department of Anatomy, Cell Biology and Physiological Sciences, American University of Beirut, Beirut, 11-0236, Lebanon

Abstract: Naphthoquinones have been reported to possess a variety of pharmacological properties including antibacterial, antifungal, antiviral, anti-inflammatory, anti-artherosclerotic and anticancer effects. We have successfully synthesized a series of novel naphthoquinone acylhydrazides. The straightforward synthesis of these molecules involves a coupling reaction between 2,3-dichloro-1,4-naphthoquinone and several alkyl and aromatic hydrazides and the hydrazides of the pyrimidine nucleobases, uracil and thymine. The product hydrazides were isolated in good yields and completely characterized by spectroscopic analysis. Biological evaluation against human colon cancer HCT116 cells and human breast cancer MCF-7 cells indicated that the novel hydrazides possessed significant anticancer activity.

Keywords: 2,3-dichloro-1,4-naphthoquinone; acylhydrazide; 1,4-napththoquinone-2-acyl hydrazides; pyrimidine nucleobase. © 2017 ACG Publications. All rights reserved.