1st International Conference on Chemo and BioInformatics, ICCBIKG 2021, (462-465)
AUTHOR(S) / АУТОР(И): Žiko B. Milanović, Edina H. Avdović, Marko R. Antonijević, Zoran S. Marković
E-ADRESS / Е-АДРЕСА: firstname.lastname@example.org , email@example.com, firstname.lastname@example.org
ABSTRACT / САЖЕТАК:
In this study, the mechanisms of antiradical activity of the previously synthesized 4,7- dihydroxycoumarin derivative:(E)-3-(1-((4-hydroxyphenyl)amino)ethylidene)-2,4- dioxochroman-7-yl acetate (A-4OH) according to the series of chloromethylperoxy radicals: OOCH2Cl (chloromethylperoxy), OOCHCl2 (dichloromethylperoxy) and OOCCl3 (trichloromethyl peroxy) were investigated. To assess the mechanisms of antiradical activity of A-4OH against chloromethylperoxy radicals, the following mechanistic pathways were examined: Hydrogen Atom Transfer (HAT), Single-Electron Transfer followed by Proton Transfer (SET-PT), and Radical Adduct Formation (RAF). The investigations were performed in water using sophisticated computational methods. The results of the study show that the activity against selected radicals decreases in series •OOCCl3 > •OOCHCl2 > •OOCH2Cl. The results of thermodynamic and kinetic parameters indicate that A-4OH inactivates selected radicals via the HAT mechanism.
KEY WORDS / КЉУЧНЕ РЕЧИ:
4,7-dihydroxycoumarin, antiradical capacity, DFT.
REFERENCES / ЛИТЕРАТУРА:
- Z. M. Nofal, M. I. El-Zahar, A. El-Karim, Novel coumarin derivatives with expected biological activity. Molecules, 5 (2000) 99-113.
- C. Kontogiorgis, D. Hadjipavlou-Litina, Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidant agents. Journal of Enzyme Inhibition and Medicinal Chemistry, 18 (2003) 63-69.
- J. C. Pan, W. F. Wang, W. Z. Lin, C. Y. Lu, Z.H. Han, S. D. Yao, N. Y. Lin, Interaction of hydroxycinnamic acid derivatives with the Cl3COO radical: a pulse radiolysis study. Freeradical research, 30 (1999) 241-245.
- Ž. B. Milanović, Z. S. Marković, D. S. Dimić, O. R. Klisurić, I. D.Radojević, D. S. Šeklić, N. Živanović, J. D. Marković, M. Radulović, E. H. Avdović, Synthesis, structural characterization, biological activity and molecular docking study of 4,7- dihydroxycoumarin modified by aminophenol derivatives. Comptes Rendus. Chimie, 24 (2021) 215-232.
- J. M. Frisch et al. Gaussian 09, Gaussian, Inc., Wallingford, CT, 2009.
- Ž.Milanović, J. Tošović, S. Marković, Z. Marković, Comparison of the scavenging capacities of phloroglucinol and 2, 4, 6-trihydroxypyridine towards HO radical: A computational study. RSC Advances, 10 (2020) 43262-43272.