Synthesis, antioxidant, and molecular docking of new fluorescent (4-alkoxyphenyl)-nitrothiophene compounds.

Abstract

New fluorescent 4-alkoxyphenyl-nitrothiophene compounds 4a-d bearing diverse alkoxyl tails are described. The synthetic strategy was simply accomplished by alkali-assisted alkylation of 4-(5-nitrothiophen-2-yl)phenol (3) with propyl, hexyl, nonyl, and/or dodecyl iodide. The molecular structures were determined using infrared (IR), 1 H NMR, and mass spectroscopy. Ultraviolet-visible (UV-vis) absorption and emission spectra of the produced 4-alkoxyphenyl-nitrothiophenes revealed considerable extinction coefficients, which were shown to be controlled by the thiophene bridge in conjugation with the alkoxy donor moiety. It was found that the maximum absorbance wavelength was affected by the alkoxyl group-bonded substituents. The antioxidant efficiency obtained from the 4-alkoxyphenyl-nitrothiophene hybrids was excellent compared with that widely used drugs [butylated hydroxytoluene (BHT) and vitamin C]. Unlike 2-(4-[dodecyloxy]phenyl)-5-nitrothiophene hybrid 4d, which has made solid claims about the good effect of its reference drugs and vitamins, Docking investigations of the prepared 4-alkoxyphenyl-nitrothiophene hybrids towards the selected 5IKQ protein revealed impressive coordination and antioxidant effectiveness.