From (2,3-dihydro-1H-perimidin-2-yl)-phenyl,
the substitution of OH group in ortho or para position on the phenyl ring,
allows us to synthesize the studied compounds. These three compounds have been characterized by conventional
spectroscopic methods (NMR and MS). The interest of this work is to review the
antioxidant activity of our compounds. The antioxidant activity screening carried
out according to FRAP and DPPH methods revealed significant anti-free radical
properties for compounds 1 and 2 even at low concentrations. In contrast to the
compound 2, compound 3 for which the OH group is substituted in para position has the lowest activity in both cases. Therefore the para position seems to be the least
sensitive position to increase the antioxidant activity of this pharmacophore.
Bartosz, G. (2003) Generation of Reactive Oxygen Species in Biological Systems. Comments on Toxicology, 9, 5-21. https://doi.org/10.1080/08865140302420
[3]
Montagnier, L., Olivier, R. and Pasquier, C. (1997) Oxidative Stress in Cancer, AIDS and Neurodegenerative Diseases. CRC Press, Boca Raton, 546.
https://doi.org/10.1201/9781482292213
[4]
Smietana, M., Clayette, P., Mialocq, P., Vasseur, J.-J. and Oiry, J. (2008) Synthesis of new N-isobutyryl-L-cysteine/MEA Conjugates: Evaluation of Their Free Radical- Scavenging, Activities and Anti-HIV Properties in Human Macrophages. Bioorganic Chemistry, 36, 133-140. https://doi.org/10.1016/j.bioorg.2008.02.001
[5]
Velázquez, I., Plaud, M., Wojna, V., Skolasky, R., Laspiur, J.P. and Meléndez, L.M. (2009) Antioxidant Enzyme Dysfunction in Monocytes and CSF of Hispanic Women with HIV Associated Cognitive Impairment. Journal of Neuroimmunology, 206, 106- 111. https://doi.org/10.1016/j.jneuroim.2008.10.013
[6]
Hebert-Schuster, M., Borderie, D., Grange, P.A., Lemarechal, H., Kavian, N., Batteux, F. and Dupin, N. (2011) Syphilis, Stress Oxydant et Statut Antioxydant. Annales de Dermatologie et de Vénéréologie, 138, A251-A252.
https://doi.org/10.1016/j.annder.2011.10.304
[7]
Rodrigo, R. and Bosco, C. (2006) Oxidative Stress and Protective Effects of Polyphenols: Comparative Studies in Human and Rodent Kidney. A Review. Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology, 142, 317-327.
https://doi.org/10.1016/j.cbpc.2005.11.002
[8]
Montazerifar, F., Hashemi, M., Karajibani, M. and Dikshit, M. (2010) Natural Antioxidants and Oxidative Stress Markers in Hemodialysis Patients. Hong Kong Journal of Nephrology, 12, 57-61. https://doi.org/10.1016/S1561-5413(10)60013-0
[9]
Nanda, N.K. and Das, B.S. (2000) Presence of Pro-Oxidants in Plasma of Patients Suffering from Falciparum Malaria. Transactions of the Royal Society of Tropical Medicine and Hygiene, 94, 684-688. https://doi.org/10.1016/S0035-9203(00)90233-5
[10]
Gülçin, I.V., Mshvildadze, A. and Gepdiremen, R. (2006) Screening of Antiradical and Antioxidant Activity of Monodesmosides and Crude Extract from Leontice smirnowii Tuber. Phytomedicine, 13, 343-351.
https://doi.org/10.1016/j.phymed.2005.03.009
[11]
Dzieduszycka, M., Martelli, S., Arciemiuk, M., Bontemps-Gracz, M.M., Kupiec, A. and Borowski, E. (2002) Effect of Modification of 6-[(Aminoalkyl)amino]-7H- benzo[e]-perimidin-7-ones on Their Cytotoxic Activity Toward Sensitive and Multidrug Resistant Tumor Cell Lines. Synthesis and Biological Evaluation. Bioorganic & Medicinal Chemistry, 10, 1025-1035.
https://doi.org/10.1016/S0968-0896(01)00358-3
[12]
Blois, M.S. (1958) Antioxidant Determinations by the Use of a Stable Free Radical. Nature, 181, 1199-1200. https://doi.org/10.1038/1811199a0
[13]
Bu, X., Deady, L.W., Finlay, G.J., Baguley, B.C. and Denny, W.A.J. (2001) Synthesis and Cytotoxic Activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-Oxo-7H-benzo [e]perimidine Derivatives. Journal of Medicinal Chemistry, 44, 2004-2014.
https://doi.org/10.1021/jm010041l
[14]
Starshikoy, N.M. and Pozharskii, F.T. (1975) Synthesis of 2-(5-halogeno-2-f uryl)- 2,3-dihydroperimidines. Chemistry of Heterocyclic Compounds, 9, 922-924.
https://doi.org/10.1007/BF00471584
[15]
Padmanabhan, P. and Jangle, S.N. (2012) Evaluation of DPPH Radical Scavenging Activity and Reducing Power of Four Selected Medicinal Plants and Their Combinations. International Journal of Pharmaceutical Sciencesand Drug Research, 4, 143-146.
[16]
Popovici, C., Saykova, I. and Tylkowsk, B. (2009) Evaluation de l’activité antioxydant des composés phénoliques par la réactivité avec le radical libre DPPH. Revue de Génie Industriel, 4, 25-39.
[17]
Molyneux, P. and Songklanakarin, J. (2004) The Use of the Stable Free Radical Diphenylpicrylhydrazyl (DPPH) for Estimating Antioxidant Activity. Sciences Technology, 26, 211-219.
[18]
Maataoui, B.S., Myene, A. and Hilali, S. (2006) Activités antiradicalaires d’extraits de jus de fruits du figuier de barbarie (Opuntia ficus indica). Lebanese Science Journal, 7, 3-8.
[19]
Lopes-Lutz, D., Alviano, C., Alviano, P. and Kolodziejczyk, P. (2008) Screening of Chemical Composition, Antimicrobial and Antioxidant Activities of Artemisia Essential Oils. Phytochemistry, 69, 1732-1738.
https://doi.org/10.1016/j.phytochem.2008.02.014
[20]
Athamena, S., Chalghem, I., Kassah-Laouar, A., Laroui, S. and Khebri, S. (2010) Activiteanti-Oxydante et antimicrobienne d’extraits de Cuminum cyminum L. Lebanese Science Journal, 11, 69-81.
[21]
Bougandoura, N. and Bendimerad, N. (2013) Evaluation de l’activité antioxydante des extraits aqueux et méthanolique de Saturejacalamintha ssp. nepeta(L.) Briq. Nature &Technologie, 9, 14-19.
[22]
Benzie, I.F. and Strain, J.J. (1996) The Ferric Reducing Ability of Plasma (FRAP) as a Measure of “Antioxidant Power”: The FRAP Assay. Analytical Biochemistry, 239, 70-76. https://doi.org/10.1006/abio.1996.0292
[23]
Sanchez-Pulido, L., Diffley, J.F.X. and Ponting, C.P. (2010) Homology explains the functional similarities of Treslin/Ticrr and Sld3. Current Biology, 20, R509-R510.
https://doi.org/10.1016/j.cub.2010.05.021
[24]
Silverstein, R.M., Webster, F.X. and Kiemle, D.J. (2016) Identification Spectrométrique de composés Organiques. 3e éd, De Boeck Supérieur, Louvain-la-Neuve, 145-150.