QSAR and mechanisms of radical scavenging activity of phenolic and anilinic compounds using structural, electronic, kinetic, and thermodynamic parameters

Medicinal Chemistry Research

Volumn 24, Issue 3, 2015, Pages 987-998

  Ali, Hussein M ^a,c   Ali, Isra H ^b  

^a Ain Shams University   (Egypt)

^b AMERICAN UNIVERSITY IN CAIRO   (Egypt)

^c IMAM ABDULRAHMAN BIN FAISAL UNIVERSITY   (Saudi Arabia)

Author keywords

Antioxidant activity; Bond dissociation energy; Phenols and anilines; QSAR; Radical scavenging mechanisms; Structural features

Indexed keywords

EID: 84939897679     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-014-1174-y     Document Type: Article

References (40)

1. Ali HM, El-Qurashi MAM (1998) Synthesis and application of some dianilinosilanes, bis (trimethylsilyl) phenylenediamines and dialkyl benzo-1,3,2-diazasilolines as antioxidants. Phosphorus Sulfur Silicon 134(135):521-529
2. Ali HM, Abo-Shady A, Sharaf Eldeen HA, Soror HA, Shousha WG, Abdel-Barry OA, Saleh AM (2013) Structural features, Kinetics and SAR study of radical scavenging and antioxidant activities of phenolic and anilinic compounds. Chem Cent J 7:53-61
3. Amić D, Lučić B (2010) Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids. Bioorg Med Chem 18:28-35
4. Amorati R, Valgimigli L (2012) Modulation of the antioxidant activity of phenols by non-covalent interactions. Org Biomol Chem 10:4147-4158
5. Amorati R, Pedulli GF, Cabrini L, Zambonin L, Landi L (2006) Solvent and pH effects on the antioxidant activity of caffeic and other phenolic acids. J Agric Food Chem 54:2932-2937
6. Bondet V, Brand-Williams W, Berset C (1997) Kinetics and mechanisms of antioxidant activity using the DPPH free radical method. Food Sci Technol 30:609-615
7. Breese KD, Lamèthe J-F, DeAmitt C (2000) Improving synthetic hindered phenol antioxidants: learning from vitamin E. Polym Degrad Stab 70:89-96
8. Castañedo-ovando A, Pacheco-Hernàndez MD, Pàez-Henàndez ME, Rodríguez JA, Galàn-Vidal CA (2009) Chemical studies of anthocyanins: a review. Food Chem 113:859-871
9. Cheng Z, Ren J, Li Y, Chang W, Chen Z (2002) Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by quantitative structure and activity relationship. Bioorg Med Chem 10:4067-4073
10. Cheng Z, Ren J, Li Y, Chang W, Chen Z (2003) Establishment of a quantitative structure-activity relationship model for evaluating and predicting the protective potentials of phenolic antioxidants on lipid peroxidation. J Pharm 92:475-484
11. De Pinedo AT, Peňalver P, Morales JC (2007) Synthesis and evaluation of new phenolic-based antioxidants: structure-activity relationship. Food Chem 103:55-61
12. Foti M, Ruberto G (2001) Kinetic solvent effects on phenolic antioxidants determined by spectroscopic measurements. J Agric Food Chem 49:342-348
13. Foti MC, Barclay LRC, Ingold KU (2002) The role of hydrogen bonding on the H-atom-donating abilities of catechols and naphthalene diols and on a previously overlooked aspect of their infrared spectra. J Am Chem Soc 124:12881-12888
14. Foti MC, Daquino C, DiLabio GA, Ingold KU (2008a) A meta effect in nonphotochemical processes: the homolytic chemistry of m-methoxyphenol. J Org Chem 73:2408-2411 ibid (2008) J Org Chem 73: 7440-7440
15. Foti MC, Daquino C, Mackie ID, DiLabio GA, Ingold KU (2008b) Reaction of phenols with the 2,2-diphenyl-1-picrylhydrazyl radical. Kinetics and DFT calculations applied to determine ArO-H bond dissociation enthalpies and reaction mechanism. J Org Chem 73:9270-9282
16. Gizdavic-Nikolaidis M, Travas-Sejdic J, Kilmartin PA, Bowmaker GA, Cooney RP (2004) Evaluation of antioxidant activity of aniline and polyaniline. Curr Appl Phys 4:343-346
17. Gizdavic-Nikolaidis M, Kilmartin PA, Travas-Sejdic J, Cooney RP, Bowmaker GA (2005) Magnetic response studies of aniline oligomers formed in the reaction of aniline with 1,1-diphenyl-2-picrylhydrazyl. Appl Magn Reson 29:729-739
18. Halliwell B, Gutteridge JMC (1999) Free radicals in biology and medicine, 3rd edn. Oxford University Press, Midsomer Norton
19. Halliwell B, Gutteridge JMC, Arouma OI (1987) The deoxyribose method: a simple "test-tube" assay for determination of rate constants for reactions of hydroxyl radicals. Anal Biochem 165:215-219
20. Hansch C, Leo A (1995) Exploring QSAR fundamental and applications in chemistry and biology. American Chemical Society, Washington, DC
21. Huang D, Ou B, Prior RL (2005) The chemistry behind antioxidant capacity assays. J Agric Food Chem 53:1841-1856
22. Jonsson M, Lind J, Eriksen TE, Merenyi G (1993) O-H bond strengths and one-electron reduction potentials of multisubstituted phenols and phenoxyl radicals. Predictions using free energy relationships. J Chem Soc, Perkin Trans II:1567-1568
23. Kajiyama T, Ohkatsu Y (2001) Effect of para-substituents of phenolic antioxidants. Polym Degrad Stab 71:445-452
24. Krishnaiah D, Sarbatly R, Nithyanandam R (2011) A review of the antioxidant potential of medicinal plant species. Food Bioprod Process 89:217-233
25. Lien EJ, Ren S, Bui H-H, Wang R (1998) Quantitative structure-activity relationship analysis of phenolic antioxidants. Free Radic Biol Med 26:285-294
26. Lucarini M, Pedulli GF (1994) Bond dissociation enthalpy of α-tocopherol and other phenolic antioxidants. J Org Chem 59:5063-5070
27. Lucarini M, Pedulli GF (2010) Free radical intermediates in the inhibition of the autoxidation reaction. Chem Soc Rev 39:2106-2119
28. Marteau C, Nardello-Rataj V, Favierc D, Aubry J-M (2013) Dual role of phenols as fragrances and antioxidants: mechanism, kinetics and drastic solvent effect. Flavour Fragr J 28:30-38
29. Mitra I, Saha A, Roy K (2012) In silico development, validation and comparison of predictive QSAR models for lipid peroxidation inhibitory activity of cinnamic acid and caffeic acid derivatives using multiple chemometric and cheminformatics tools. J Mol Model 18:3951-3967
30. Molyneux P (2004) The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J Sci Technol 26:211-219
31. Ordoudi SA, Tsimidou MZ, Vafiadis AP, Bakalbassis EG (2006) Structure-DPPH. Scavenging activity relationships; parallel study of catechol and guaiacol acid derivatives. J Agric Food Chem 54:5763-5768
32. Rastija V, Medić-Sarić M (2009) QSAR study of antioxidant activity of wine polyphenols. Eur J Med Chem 44:400-408
33. Sarkar A, Middya TR, Jana AD (2012) A QSAR study of radical scavenging antioxidant activity of a series of flavonoids using DFT based quantum chemical descriptors: the importance of group frontier electron density. J Mol Model 18:2621-2631
34. Takahashi N, Tamagawa K, Kubo Y, Fukui T, Wakabayashi H, Honda T (2003) Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation. Bioorg Med Chem 11:3255-3260
35. Tyrakowska B, Soffers AEMF, Szymusiak H, Boeren S, Boersma MG, Lemanska K, Vervoort J, Rietjens IM (1999) TEAC antioxidant activity of 4-hydroxybenzoates. Free Radic Biol Med 27:1427-1436
36. Vafiadis AP, Bakalbassis EG (2005) A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals. Chem Phys 316:195-204
37. Wanasundara PKJPD, Shahidi F (2005) Antioxidants: science, technology, and applications. In: Shahidi F (ed) Bailey's industrial oil and fat products, vol 6, 6th edn. Wiley, New York, pp 431-489
38. Yaday AK, Thakur J, Prakash O, Khan F, Saikia D, Gupta M (2013) Screening of flavonoids for antitubercular activity and their structure-activity relationships. Med Chem Res 22:2706-2716
39. Yamagami C, Akamatsu M, Motohashi N, Hamada S, Tanahashi T (2005) Quantitative structure-activity relationship studies for antioxidant hydroxybenzalacetones by quantum chemical- and 3-D-QSAR (CoMFA) analyses. Bioorg Med Chem Lett 15:2845-2850
40. Zhang H-Y (2005) Structure-activity relationship and rational design strategies for radical scavenging antioxidants. Curr Comput Aided Drug Design 1:257-273