Synthesis, Characterization, and Pharmacokinetic Study of Novel 1,2,3-Triazolo/amido Hydroquinone Derivatives as Anticancer and Antibacterial Agents

In the present study, novel 1,2,3-triazolo/amido derivatives of hydroquinone have been prepared and tested for the anticancer and antibacterial potential. The structures of the synthesized derivatives were established by various analytical techniques. One of the products, 2-(4-{[1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl]methoxy}phenoxy)acetic acid, showed promising cytotoxicity (IC₅₀ 0.92, 1.72, and 3.56 μM against MCF-7, HepG2 and SKOV3 cells, respectively), close to that of the standard drug doxorubicin. In terms of the antibacterial activity, 2-(4-{[1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]methoxy}phenoxy)acetic acidexhibited the highest activity against S. aureus (MIC 25 μg/mL) and E. coli (MIC 50 μg/mL), which was close to the inhibitory activity of amoxicillin. The in silico ADME study showed that all the synthesized hydroquinone derivatives followed the Lipinski’s rule with zero violations, are lipophilic and flexible and have good gastrointestinal absorption and poor permeability through the blood brain barrier.