Abstract
The target 2-phenoxy[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines (1–6) was previously synthesized and fully characterized. In the present study, the antioxidant activity of compounds 1–6 was evaluated using 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging, ferric reducing antioxidant power, 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and reducing power capacity assays. The findings showed that at fifth of the used concentration (0.1 mg/mL), six of the examined pyridotriazolopyrimidines (6d–6h) are superior to the compounds as they displayed the highest capacity to scavenge DPPH, ABTS and free radicals when compared to the standard agent, butylated hydroxytoluene. Theoretical calculations based on density functional theory study together with structural modifications of the targets provided valuable clarifications regarding the requirements to synthesize more active target compounds against free radicals.
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References
Abuelizz HA, Iwana NI, Ahmad R, Anouar EH, Marzouk M, Al-Salahi R (2019a) Synthesis, biological activity and molecular docking of new tricyclic series as α-glucosidase inhibitors. BMC Chem 13:52. https://doi.org/10.1186/s13065-019-0560-4
Abuelizz HA, Taie HAA, Marzouk M, Al-Salahi R (2019b) Synthesis and antioxidant activity of 2-methylthio-pyrido[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines. Open Chem 17:823–830. https://doi.org/10.1515/chem-2019-0092
Akbas E, Ergan E, Sahin E, Ekin S, Cakir M, Karakus Y (2018) Synthesis, characterization, antioxidant properties and DFT calculation of some new pyrimidine derivatives. Phosphorus Sulfur Silicon Relat Elem. https://doi.org/10.1080/10426507.2018.1550489
Almehizia AA, Abuelizz HA, Taie HAA, ElHassane A, Marzouk M, Al-Salahi R (2019) Investigation the antioxidant activity of benzo[g]triazoloquinazolines correlated with a DFT study. Saudi Pharm J 27:133–137. https://doi.org/10.1016/j.jsps.2018.09.006
Al-Salahi R, Anouar EH, Marzouk M, Taie HA, Abuelizz HA (2018) Screening and evaluation of antioxidant activity of some 1,2,4-triazolo[1,5-a]quinazoline derivatives. Future Med Chem 10:379–390. https://doi.org/10.4155/fmc-2017-0224
Al-Salahi R, Taie HAA, Bakheit AB, Marzouk M, Almehizia A, Herqash R, Abuelizz HA (2019) Antioxidant activities and molecular docking of 2-thioxobenzo[g] quinazoline derivatives. Pharmacol Rep 71:695–700. https://doi.org/10.1016/j.pharep.2019.04.003)
Chan KW, Khong NM, Iqbal S, Umar IM, Ismail M (2012) Antioxidant property enhancement of sweet potato flour under simulated gastrointestinal pH. Int J Mol Sci 13:8987–8997. https://doi.org/10.3390/ijms13078987
Guerra-Vargas MA, Rosales-Hernández MC, Martínez-Fonseca N, Padilla-Martínez I, Fonseca-Sabater Y, Martínez-Ramos F (2018) 2-Acetyl-4-aminoresorcinol derivatives: synthesis, antioxidant activity and molecular docking studies. Med Chem Res 27:1186–1197. https://doi.org/10.1007/s00044-018-2139-3
Gurer-Orhan H, Karaaslan C, Ozcan S, Firuzi O, Tavakkoli M, Saso L, Suzen S (2016) Novel indole-based melatonin analogues: evaluation of antioxidant activity and protective effect against amyloid β-induced damage. Bioorg Med Chem 24:1658–1664. https://doi.org/10.1016/j.bmc.2016.02.039
Khokra SL, Khan SA, Thakur P, Chowdhary D, Ahmad A, Husain A (2016) Synthesis, molecular docking and potential antioxidant activity of di/trisubstituted pyridazinone derivatives. J Chin Chem Soc 63:739–750. https://doi.org/10.1002/jccs.201600051
Liu Q, Tang GY, Zhao CN, Gan RY, Li HB (2019) Antioxidant activities, phenolic profiles, and organic acid contents of fruit vinegars. Antioxidants 8(4):78. https://doi.org/10.3390/antiox8040078
Pham-Huy LA, He H, Pham-Huy C (2008) Free radicals, antioxidants in disease and health. Int J Biomed Sci 4:89–96 (PMC3614697)
Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 26:1231–1237. https://doi.org/10.1016/s0891-5849(98)00315-3
Roesslein M, Hirsch C, Kaiser J-P, Krug HF, Wick P (2013) Comparability of in vitro tests for bioactive nanoparticles: a common assay to detect reactive oxygen species as an example. Int J Mol Sci 14:24320–24337. https://doi.org/10.3390/ijms141224320
Silva VLM, Elguero J, Silva AMS (2018) Current progress on antioxidants incorporating the pyrazole core. Eur J Med Chem 156:394–429. https://doi.org/10.1016/j.ejmech.2018.07.007
Teng Y, Li X, Yang K, Li X, Zhang Z, Wang L, Deng Z, Song B, Yan Z, Zhang Y, Lu K, Yu P (2017) Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers. Eur J Med Chem 125:335–345. https://doi.org/10.1016/j.ejmech.2016.09.024
Thanan R, Oikawa S, Hiraku Y (2015) Oxidative stress and its significant roles in neurodegenerative diseases and cancer. Int J Mol Sci 16:193–217. https://doi.org/10.3390/ijms16010193
Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J (2007) Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 39:44–48. https://doi.org/10.1016/j.biocel.2006.07.001
Wang J, Xia F, Jin WB, Guan JY, Zhao H (2016) Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues. Bioorg Chem 68:214–218. https://doi.org/10.1016/j.bioorg.2016.08.008
Yapati H, Devineni SR, Chirumamilla S, Kalluru S (2016) Synthesis, characterization and studies on antioxidant and molecular docking of metal complexes of 1-(benzo[d]thiazol-2-yl)thiourea. J Chem Sci 128:43–51. https://doi.org/10.1007/s12039-015-0999-3
Zhu ZY, Pan LC, Yun-Tang, Zhang YM (2018) Structural analysis and antioxidant activity of the glycoside from Imperial Chrysanthemum. Bioorg Med Chem Lett 28:1581–1590. https://doi.org/10.1016/j.bmcl.2018.03.059
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The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the research group Project No. RG-1439-011.
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Abuelizz, H.A., Anouar, E., Marzouk, M. et al. DFT study and radical scavenging activity of 2-phenoxypyridotriazolo pyrimidines by DPPH, ABTS, FRAP and reducing power capacity. Chem. Pap. 74, 2893–2899 (2020). https://doi.org/10.1007/s11696-020-01126-0
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DOI: https://doi.org/10.1007/s11696-020-01126-0