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

Autor: Yehye WA; Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, Kuala Lumpur 50603, Malaysia. wdabdoub@um.edu.my., Abdul Rahman N; Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. noorsaadah@um.edu.my.; Drug Design and Development Research Group, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. noorsaadah@um.edu.my., Saad O; Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia. omar79@siswa.um.edu.my., Ariffin A; Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. azhar70@um.edu.my., Abd Hamid SB; Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, Kuala Lumpur 50603, Malaysia. sharifahbee@um.edu.my., Alhadi AA; Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. aaalhamadani@yahoo.com.; Drug Design and Development Research Group, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. aaalhamadani@yahoo.com., Kadir FA; Division of Human Biology, School of Medicine, International Medical University, Kuala Lumpur 57000, Malaysia. FarqadAbdulhadi@imu.edu.my., Yaeghoobi M; Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. m.yaeghoobi@gmail.com.; Drug Design and Development Research Group, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. m.yaeghoobi@gmail.com., Matlob AA; Department of Environmental Technology, College of Environment, Mosul University, Mosul 41001, Iraq. matlob58@yahoo.com.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2016 Jun 28; Vol. 21 (7). Date of Electronic Publication: 2016 Jun 28.
DOI: 10.3390/molecules21070847
Abstrakt: 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.
Databáze: MEDLINE