Synthesis of new α-aminophosphonate derivatives incorporating benzimidazole, theophylline and adenine nucleobases using l-cysteine functionalized magnetic nanoparticles (LCMNP) as magnetic reusable catalyst: evaluation of their anticancer properties

Abstract

A new class of structurally diverse α-aminophosphonate derivatives containing benzimidazole, theophylline and adenine heterocycles were synthesized using a simple and efficient strategy. This class of α-aminophosphonates was synthesized using the reaction of synthetic aldehydes containing nucleobases, amines and diethyl phosphonate using L-cysteine functionalized magnetic nanoparticles (LCMNP) as catalyst. The aldehyde derivatives containing benzimidazole, theophylline and adenine nucleobases were synthesized using the reaction of a bromo-substituted aldehyde derived from isovanillin and 4-hydroxy benzaldehyde. The LCMNP catalyst was found to be an efficient magnetic reusable catalyst for synthesis of this class of α-aminophosphonates under mild and clean conditions. This method is introduced as a suitable approach for the synthesis of new α-aminophosphonate derivatives containing nucleobases which have potential biological activity. When the anticancer properties of a selected group of these synthetic ligands were evaluated, they indicated poor activity compared to cisplatin against the Jurkat cancer cell line.