One pot synthesis of N-7 alkylated xanthine derivatives and their exploration as antioxidant, antimicrobial and nematicidal agents

The widespread presence of economically dominant pathogens has significantly hindered agricultural growth and productivity by affecting the quality and yield of crops. The recent deregistration of essential bactericides and nematicides have underscored the urgency for the development of novel agrochemical candidates. In response, N-7 alkylated xanthine derivatives were synthesized using various alkylbromides and characterized with the help of various spectroscopic techniques. The synthesized derivatives were explored for antioxidant, antibacterial, antifungal and antinemic properties. A comprehensive evaluation of antioxidant potential of synthesized compounds utilizing various models revealed that compound 7-decyl-1H-purine-2,6-(3H,7H)-dione (2j) exhibited strong antioxidant potential due to enhancement of electron-donating characterin reference to ascorbic acid. Furthermore, evaluation of antimicrobial activity against Dickeya sp., Xanthomonas campestris and Fusarium oxysporum, and antinemicactivity against Meloidogyne incognita, demonstrated that compound (2j), among other tested compounds, displayed noteworthy inhibitory activity against these pathogens as compared to reference drugs i.e. ciprofloxacin, gentamycin (antimicrobial activity) and carbofuran (antinemic activity). Also, in silico investigations were performed aiming for acetylcholine esterase enzyme inhibition activities to recognize novel interactions of the tested compounds with target binding sites of Meloidogyne incognita. The promising in vitro results warrant further validation under in vivo and field conditions. This research offers valuable insights that these compounds can serve as key precursors for future development of agrochemical agents for managing biotic stresses and improving crop productivity.