Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids
2017
Аутори
Mihailović, NevenaMarković, Violeta
Matić, Ivana Z.
Stanisavljević, Nemanja S.
Jovanović, Živko S.
Trifunović, Snežana S.
Joksović, Ljubinka
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Eight 1,3,4-oxadiazole derivatives containing phenolic acid moieties (7a-h) and eight of their diacylhydrazine precursors (6a-h) were synthesized, characterized using spectroscopic methods and examined by scavenging of stable DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals. The most potent phenolic 1,3,4-oxadiazoles showed better DPPH scavenging activity in comparison with their corresponding diacylhydrazine precursors as a result of participation of both aromatic rings and a 1,3,4-oxadiazole moiety in resonance stabilization of the formed phenoxyl radical. Four diacylhydrazines (6d, 6e, 6g, and 6h) and four 1,3,4-oxadiazoles (7d, 7e, 7g and 7h) with the best DPPH scavenging activity, were chosen for further evaluation of their antioxidant potential through various assays. The investigated compounds exerted pronounced ABTS radical scavenging capacity, moderate to good H2O2 scavenging properties and strong ferric ion reducing capacity. Further in vitro evaluation of the antioxidant proper...ties of the most active compounds demonstrated their protective effects in normal lung fibroblasts MRC-5 against hydrogen peroxide induced oxidative stress. Diacylhydrazine 6h increased two times the activity of glutathione peroxidase in treated cells in comparison with a control sample and did not affect the superoxide dismutase activity.
Извор:
RSC Advances, 2017, 7, 14, 8550-8560Издавач:
- Royal Soc Chemistry, Cambridge
Финансирање / пројекти:
- Синтеза, моделовање, физичко-хемијске и биолошке особине органских једињења и одговарајућих комплекса метала (RS-172016)
- Модификатори биолошког одговора у физиолошким и патолошким стањима (RS-175011)
- Молекуларни механизми одговора биљака на абиотички стрес-улога транскрипционих фактора и малих РНК и анализа генетичког диверзитета биљних култура од интереса за пољопривреду и биотехнологију (RS-173005)
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/2980
DOI: 10.1039/c6ra28787e
ISSN: 2046-2069
WoS: 000393758700055
Scopus: 2-s2.0-85011063370
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Mihailović, Nevena AU - Marković, Violeta AU - Matić, Ivana Z. AU - Stanisavljević, Nemanja S. AU - Jovanović, Živko S. AU - Trifunović, Snežana S. AU - Joksović, Ljubinka PY - 2017 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2398 AB - Eight 1,3,4-oxadiazole derivatives containing phenolic acid moieties (7a-h) and eight of their diacylhydrazine precursors (6a-h) were synthesized, characterized using spectroscopic methods and examined by scavenging of stable DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals. The most potent phenolic 1,3,4-oxadiazoles showed better DPPH scavenging activity in comparison with their corresponding diacylhydrazine precursors as a result of participation of both aromatic rings and a 1,3,4-oxadiazole moiety in resonance stabilization of the formed phenoxyl radical. Four diacylhydrazines (6d, 6e, 6g, and 6h) and four 1,3,4-oxadiazoles (7d, 7e, 7g and 7h) with the best DPPH scavenging activity, were chosen for further evaluation of their antioxidant potential through various assays. The investigated compounds exerted pronounced ABTS radical scavenging capacity, moderate to good H2O2 scavenging properties and strong ferric ion reducing capacity. Further in vitro evaluation of the antioxidant properties of the most active compounds demonstrated their protective effects in normal lung fibroblasts MRC-5 against hydrogen peroxide induced oxidative stress. Diacylhydrazine 6h increased two times the activity of glutathione peroxidase in treated cells in comparison with a control sample and did not affect the superoxide dismutase activity. PB - Royal Soc Chemistry, Cambridge T2 - RSC Advances T1 - Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids VL - 7 IS - 14 SP - 8550 EP - 8560 DO - 10.1039/c6ra28787e ER -
@article{ author = "Mihailović, Nevena and Marković, Violeta and Matić, Ivana Z. and Stanisavljević, Nemanja S. and Jovanović, Živko S. and Trifunović, Snežana S. and Joksović, Ljubinka", year = "2017", abstract = "Eight 1,3,4-oxadiazole derivatives containing phenolic acid moieties (7a-h) and eight of their diacylhydrazine precursors (6a-h) were synthesized, characterized using spectroscopic methods and examined by scavenging of stable DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals. The most potent phenolic 1,3,4-oxadiazoles showed better DPPH scavenging activity in comparison with their corresponding diacylhydrazine precursors as a result of participation of both aromatic rings and a 1,3,4-oxadiazole moiety in resonance stabilization of the formed phenoxyl radical. Four diacylhydrazines (6d, 6e, 6g, and 6h) and four 1,3,4-oxadiazoles (7d, 7e, 7g and 7h) with the best DPPH scavenging activity, were chosen for further evaluation of their antioxidant potential through various assays. The investigated compounds exerted pronounced ABTS radical scavenging capacity, moderate to good H2O2 scavenging properties and strong ferric ion reducing capacity. Further in vitro evaluation of the antioxidant properties of the most active compounds demonstrated their protective effects in normal lung fibroblasts MRC-5 against hydrogen peroxide induced oxidative stress. Diacylhydrazine 6h increased two times the activity of glutathione peroxidase in treated cells in comparison with a control sample and did not affect the superoxide dismutase activity.", publisher = "Royal Soc Chemistry, Cambridge", journal = "RSC Advances", title = "Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids", volume = "7", number = "14", pages = "8550-8560", doi = "10.1039/c6ra28787e" }
Mihailović, N., Marković, V., Matić, I. Z., Stanisavljević, N. S., Jovanović, Ž. S., Trifunović, S. S.,& Joksović, L.. (2017). Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids. in RSC Advances Royal Soc Chemistry, Cambridge., 7(14), 8550-8560. https://doi.org/10.1039/c6ra28787e
Mihailović N, Marković V, Matić IZ, Stanisavljević NS, Jovanović ŽS, Trifunović SS, Joksović L. Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids. in RSC Advances. 2017;7(14):8550-8560. doi:10.1039/c6ra28787e .
Mihailović, Nevena, Marković, Violeta, Matić, Ivana Z., Stanisavljević, Nemanja S., Jovanović, Živko S., Trifunović, Snežana S., Joksović, Ljubinka, "Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids" in RSC Advances, 7, no. 14 (2017):8550-8560, https://doi.org/10.1039/c6ra28787e . .