Synthesis, biological and electrochemical evaluation of novel nitroaromatics as potential anticancerous drugs

Abstract

Nitroaromatics i.e. 1-nitro-4-phenoxybenzene (1), 4-(4-nitrophenyloxy) biphenyl (2), 1-(4-nitrophenoxy) naphthalene (3) and 2-(4-nitrophenoxy) naphthalene (4) were synthesized by Williamson etherification and characterized by elemental analysis, FTIR, NMR ( 1 H, 13 C), UV-visible spectroscopy, mass spectrometry and single crystal X-ray diffraction analysis. Their brine shrimp cytotoxicity resulted in LD 50 values <1μg/mL indicating significant antitumor activity with IC 50 values ranging from 29.0 to 8.4μg/mL. They are highly active in protecting DNA against hydroxyl free radicals in a concentration dependent manner. Voltammetric studies showed one electron reversible reduction at a platinum electrode with diffusion coefficient (D o) values of the order ~10 -6 -10 -7 cm 2 s -1. Strong interaction with the human blood DNA through intercalative mode was contemplated through electrochemical and UV-visible spectroscopic studies which are in agreement with the conclusions drawn from biological analysis, unravelling the potential anticancerous nature of the synthesized compounds.