Chemistry of Phosphorus Ylides. Part 47. Synthesis of Organophosphorus and Selenium Pyrazolone Derivatives, Their Antioxidant Activity, and Cytotoxicity against MCF7 and HepG2

Abstract

Reaction of oxobutenyl- and oxophenylpropenyl-phenylpyrazolones with the active phosphacumulenes, iminovinylidene- and oxovinylidenetriphenylphosphoranes has led to pyranopyrazole and phosphoranylidenepyranopyrazole, respectively. Reaction of the pyrazolones with the stablized phosphonium ylides has resulted in pyrazolodienoates. Reaction of Woolin’s (diselenadiphosphetandiselenides) reagent with the pyrazole derivative substrates has resulted in formation of different phosphorus-selenium heterocyclic pyrazole derivatives such as oxaselenaphosphinin-, selenoxobutenyl-, selenidodiselenaphosphinyl-, and diselenidoselenadiphosphetanylvinyl pyrazoles. The possible reaction mechanism is considered, and structural elucidations are based on spectroscopic data. Antitumor and antioxidant activities of the new compounds have been evaluated. The structure-activity relationship (SAR) for the products is discussed.