Synthesis, Chemical Transformation and Antimicrobial Activity of a Novel Class of Nitroolefins: 1,3-Diaryl-2-nitroprop-1-enes

Abstract The synthesis of novel, biologically active 1,3-diaryl-2-nitroprop-1-enes (4) is reported. The synthesis involves condensation between aromatic aldehydes (1) and β-aryl nitroethanes (3). The chemical transformation of the nitro group in diaryl nitropropenes to a carbonyl function has resulted in a new route to the synthesis of an α-hydroxy analog (7c) of a naturally occurring 3, 3′, 4, 4′-tetramethoxy chalcone. The antimicrobial activity of the 1, 3-diaryl-2-nitroprop-1-enes (4a-j) was tested against three gram positive bacteria, two gram negative bacteria and two fungi. These compounds exhibited broad spectrum antimicrobial activity.