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Molecules 2016, 21(7), 847; doi:10.3390/molecules21070847

Rational Design and Synthesis of New, High Efficiency, Multipotent Schiff Base-1,2,4-triazole Antioxidants Bearing Butylated Hydroxytoluene Moieties

1
Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, Kuala Lumpur 50603, Malaysia
2
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
3
Drug Design and Development Research Group, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
4
Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia
5
Division of Human Biology, School of Medicine, International Medical University, Kuala Lumpur 57000, Malaysia
6
Department of Environmental Technology, College of Environment, Mosul University, Mosul 41001, Iraq
*
Author to whom correspondence should be addressed.
Academic Editor: Fawaz Aldabbagh
Received: 5 June 2016 / Revised: 22 June 2016 / Accepted: 24 June 2016 / Published: 28 June 2016
(This article belongs to the Special Issue Free Radicals in Organic Synthesis)
View Full-Text   |   Download PDF [1686 KB, uploaded 28 June 2016]   |  

Abstract

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 410 were tested by the DPPH bioassay. The synthesized compounds 410 inhibited stable DPPH free radicals at a level that is 10−4 M more than the well-known standard antioxidant BHT. Compounds 810 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. View Full-Text
Keywords: butylated hydroxytoluene; PASS; 1,2,4-triazole; Schiff base; DPPH assay butylated hydroxytoluene; PASS; 1,2,4-triazole; Schiff base; DPPH assay
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Yehye, W.A.; Abdul Rahman, N.; Saad, O.; Ariffin, A.; Abd Hamid, S.B.; Alhadi, A.A.; Kadir, F.A.; Yaeghoobi, M.; Matlob, A.A. Rational Design and Synthesis of New, High Efficiency, Multipotent Schiff Base-1,2,4-triazole Antioxidants Bearing Butylated Hydroxytoluene Moieties. Molecules 2016, 21, 847.

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