Rational Design and Synthesis of New, High Efficiency, Multipotent Schiff Base-1,2,4-triazole Antioxidants Bearing Butylated Hydroxytoluene Moieties
Wageeh A Yehye,
Noorsaadah Abdul Rahman,
Omar Saad,
Azhar Ariffin,
Sharifah Bee Abd Hamid,
Abeer A. Alhadi,
Farkaad A. Kadir,
Marzieh Yaeghoobi,
Abdulsalam A. Matlob
Affiliations
Wageeh A Yehye
Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, Kuala Lumpur 50603, Malaysia
Noorsaadah Abdul Rahman
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
Omar Saad
Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia
Azhar Ariffin
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
Sharifah Bee Abd Hamid
Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, Kuala Lumpur 50603, Malaysia
Abeer A. Alhadi
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
Farkaad A. Kadir
Division of Human Biology, School of Medicine, International Medical University, Kuala Lumpur 57000, Malaysia
Marzieh Yaeghoobi
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
Abdulsalam A. Matlob
Department of Environmental Technology, College of Environment, Mosul University, Mosul 41001, Iraq
A new series of multipotent antioxidants (MPAOs), namely Schiff base-1,2,4-triazoles attached to the oxygen-derived free radical scavenging moiety butylated hydroxytoluene (BHT) were designed and subsequently synthesized. The structure-activity relationship (SAR) of the designed antioxidants was established alongside the prediction of activity spectra for substances (PASS). The antioxidant activities of the synthesized compounds 4–10 were tested by the DPPH bioassay. The synthesized compounds 4–10 inhibited stable DPPH free radicals at a level that is 10−4 M more than the well-known standard antioxidant BHT. Compounds 8–10 with para-substituents were less active than compounds 4 and 5 with trimethoxy substituents compared to those with a second BHT moiety (compounds 6 and 7). With an IC50 of 46.13 ± 0.31 µM, compound 6 exhibited the most promising in vitro inhibition at 89%. Therefore, novel MPAOs containing active triazole rings, thioethers, Schiff bases, and BHT moieties are suggested as potential antioxidants for inhibiting oxidative stress processes and scavenging free radicals, hence, this combination of functions is anticipated to play a vital role in repairing cellular damage, preventing various human diseases and in medical therapeutic applications.
