Synthesis and Biological Evaluation of a Schiff Base Appended Triazole as a Multifunctional Agent

Abstract

The present study describes the synthesis of a novel Schiff base-appended triazole (SBAT) via copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), highlighting its dual functionality in both plant development and human disease management. The structure of SBAT was confirmed using NMR, X-ray crystallography, and mass spectrometry. Biological evaluation revealed its potent antibacterial activity against E. coli (IC50 = 0.72 mg/mL), with ciprofloxacin as the reference drug. The mechanism likely involves interference with bacterial cell wall formation and oxidative stress induction. Anticancer potential was demonstrated against HeLa cells using MTT assays, where SBAT inhibited 57.45% of cell growth, possibly via ROS generation and mitochondrial dysfunction, with paclitaxel as a positive control. In plants, SBAT at 10 mg/L significantly promoted root and shoot growth, indicating cytokinin-like effects through stimulation of cell division and meristem activity. Enhanced levels of chlorophyll, carotenoids, proteins, flavonoids, and phenolics were also observed. Molecular docking studies supported its role as a plant growth regulator (binding affinity -9.1 kcal/mol with cytokinin oxidase) and as an anticancer agent (binding affinity -7.69 kcal/mol with HPV protein). Compared to existing Schiff base and triazole analogues, SBAT exhibited superior multifunctional efficacy, making it a promising candidate for integrated therapeutic and agricultural use.