Synthesis, Characterization, and Biological Evaluation of Novel Cyclohexenone Derivatives Incorporating Azo, Triazene, and Tetraazene Moieties

The new cyclohexenone derivatives have been synthesized by diazo-coupling reactions using 3,5-diphenylcyclohex-2-en-1-one (2) and hydrazone derivative 3 as versatile scaffolds. The structures of the newly synthesized compounds were smoothly elucidated based upon different spectral techniques. The new compounds which bearing azo, triazene or tetraazene moieties were evaluated as antioxidant and antimicrobial agents. The minimal inhibitory concentrations (MICs) values for the most active compounds in antibacterial activity were evaluated. Compounds 8 and 15 revealed the highest antioxidant activity with inhibition values (53.5%) and (47.8%), respectively. In the case of S. aureus, compound 10 exhibited potent antibacterial activity with (95.8%) AI. In the case of E. coli, compound 10 revealed excellent antibacterial activity with (84.6%) AI. In the case of C. albicans, compounds 10, 12 and 14 revealed the best activities with an activity index (66.7–74.1%).