Synthesis, Electrochemical, Antibacterial and Anticancer Studies on Triazole‐Bridged Pyrrolidine‐Grafted Macrocycles via [3+2] Cycloaddition of Azomethin Ylide

An efficient and regioselective synthesis of triazole bridged pyrrolidine grafted macrocycle derivatives was accomplished by O‐alkylation, followed by aldol/Wittig reaction, click reaction with salicylaldehyde and finally by intramolecular 1, 3‐dipolar cycloaddition (1,3‐DC) to with azomethin ylide. The regio‐ and stereochemical outcome of the reaction was unambiguously established by single crystal X‐ray analysis of the cycloadducts. All the synthesized macrocycles exhibit irreversible oxidation reduction signals in cyclic voltammetry. Antioxidant property and antibacterial activity against Bacillus cereus and Klebsiella pneumoniae bacteria and anticancer activity against human adenocarcinoma breast cancer cell line cells (MCF‐7) revealed that all the pyrrolidine grafted macrocycles showed activity comparable to that of the standard drug. The pyrrolidine grafted macrocycles with triazole as spacer unit has been achieved via regioselective click reaction and intramolecular 1,3‐dipolar cycloaddition of azomethin ylide. All the synthesized macrocycles exhibit comparable antibacterial, antioxidant and anticancer activity.