Fluoroquinolone-Triazole Hybrid Molecules: A Comparative Analysis of Conventional and Green Synthetic Methods, and Evaluation of Their Biological Activities

In this study, a series of 1,2,4-triazole derivatives was initially synthesized and subsequently incorporated into the fluoroquinolone scaffold via Mannich-type reactions. The reactions were conducted using conventional heating, ultrasound-assisted synthesis, and microwave irradiation techniques to determine the optimal reaction conditions. FTIR, NMR, and mass spectrometry analyses characterized the structures of the resulting compounds. Furthermore, the synthesized derivatives were assessed for their antimicrobial and antioxidant properties. Their inhibitory activities against key enzymes, urease, alpha-amylase, alpha-glucosidase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase, were also investigated, with several compounds exhibiting noteworthy bioactivity. Nearly all the synthesized hybrid compounds exhibited minimum inhibitory concentration (MIC) values comparable to standard antibacterial agents such as norfloxacin and ciprofloxacin. Except for 4-arylideneamino-1,2,4-triazole-3-one derivatives, all tested compounds demonstrated notable anti-urease activity. Furthermore, several newly synthesized molecules showed promising inhibitory effects against alpha-amylase and alpha-glucosidase enzymes.