Nitrofurantoin, the first member of the nitrofuran class of antibacterials was launched in 1953, though the exact mechanism of its action is not well understood, it is thought to undergo one or more reductions in the bacterial cells so as to generate radicals and subsequent reactive amines and cyano species which damage their deoxyribonucleic acid (DNA). Nitrofurantoin is commonly administered orally for treatment of acute or recurring uncomplicated urinary tract infections and pyelitis. To this end, 5-nitrofurfural as potential pharmacophore of nitrofuran antibacterials 8 stood out as a promising candidate in virtue of its small size, simplicity, stability, ease of synthesis (EoS) and multiple modes of action.