Synthesis, biological and electrochemical evaluation of novel nitroaromatics as potential anticancerous drugs
Muhammad Shabbir1, Zareen Akhter1, Iqbal Ahmad2
1Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
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 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) 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.
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