Synthesis of new symmetric cyclic and acyclic halocurcumin analogues typical precursors for hybridization

Abstract

It is believed that the synthesis of hybrid molecules containing different biologically relevant moieties would furnish multifunctional drugs with the possible synergism of potential importance for the treatment of cancer, diabetic and Alzheimer diseases. It was envisioned that synthesizing different cyclic and acyclic halocurcumin intermediates would furnish key precursors for hybridization. Thus, starting from vanillin (I) as a naturally occurring compound, several O-haloalkyl derivatives (IIa, IIb and III) have been synthesized and characterized. These derivatives were subjected to Knoevenagel condensation reaction with deferent acyclic and cyclic ketones to afford the corresponding symmetric halocurcumin analogues (IV–VIII). The chemical structures of the newly synthesized curcumin intermediates were confirmed with spectroscopic techniques. These analogues, having primary halogen from both sides, are typical precursors of hybrid curcumin analogues.