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

• Four new nitroaromatics were synthesized with yields around 75%.
• Voltammetric studies revealed reversible one electron transfer with Do ~ 10− 6–10− 7 cm2 s− 1.
• Biological studies have indicated significant anticancerous nature.
• Drug–DNA interaction was shown by voltammetry and UV–visible spectroscopy.
• The compound–DNA adduct formation constants were in the range of 2–8 × 104 M− 1.

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 (1H, 13C), UV–visible spectroscopy, mass spectrometry and single crystal X-ray diffraction analysis. Their brine shrimp cytotoxicity resulted in LD50 values < 1 μg/mL indicating significant antitumor activity with IC50 values ranging from 29.0 to 8.4 μg/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 (Do) values of the order ~ 10− 6–10− 7 cm2 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.

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