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Pregled bibliografske jedinice broj: 1145233

Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential


Boček, Ida; Starčević, Kristina; Novak Jovanović, Ivana; Vianello, Robert; Hranjec, Marijana
Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential // Journal of molecular liquids, 342 (2021), 117527, 14 doi:10.1016/j.molliq.2021.117527 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1145233 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential

Autori
Boček, Ida ; Starčević, Kristina ; Novak Jovanović, Ivana ; Vianello, Robert ; Hranjec, Marijana

Izvornik
Journal of molecular liquids (0167-7322) 342 (2021); 117527, 14

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
acrylonitriles ; antioxidative potential ; DFT calculations ; electrochemical oxidation potential ; imidazo[4 ; 5-b]pyridines ; solvent effects

Sažetak
We describe the synthesis of novel unsubstituted and N-substituted imidazo[4, 5-b]pyridine derived acrylonitriles, which were prepared by classical and microwave assisted organic synthesis. Their antioxidative potential was studied using spectroscopic DPPH and ABTS assays, FRAP method and electrochemical oxidation potential measurements. Targeted acrylonitriles were designed in order to study the influence of the methoxy, N, N-dimethylamino and N, N-diethylamino substituents on the antioxidative activity as well as the type of the substituent placed on the N- atom of the imidazo[4, 5-b]pyridine nuclei. The most active derivatives with significantly improved activity relative to the standard BHT, were systems substituted with the N, N-(CH3)2 group 29 and the N, N-(CH2CH3)2 group at the para position of the phenyl ring 24, 30, 32 and 34. Computational analysis revealed that investigated antioxidative features are predominantly relying on the hydrogen atom transfer properties and can be efficiently enhanced through either the N- alkylation of the imidazole nitrogen or by introducing electron-donating substituents on the distant phenyl unit, where N, N-dialkylamines prevail over methoxy groups. Absorption spectra of chosen compounds were recorded in several organic solvents to further reveal the impact of the substituent effects and solvent polarity on spectroscopic features.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4379 - Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa (AntioxPot) (Hranjec, Marijana, HRZZ - 2018-01) ( CroRIS)
HRZZ-IP-2016-06-3163 - Lipidi hrane, spol i dob u patogenezi metaboličkog sindroma (DietMetSyn) (Starčević, Kristina, HRZZ - 2016-06) ( CroRIS)

Ustanove:
Institut za medicinska istraživanja i medicinu rada, Zagreb,
Veterinarski fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com fulir.irb.hr

Citiraj ovu publikaciju:

Boček, Ida; Starčević, Kristina; Novak Jovanović, Ivana; Vianello, Robert; Hranjec, Marijana
Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential // Journal of molecular liquids, 342 (2021), 117527, 14 doi:10.1016/j.molliq.2021.117527 (međunarodna recenzija, članak, znanstveni)
Boček, I., Starčević, K., Novak Jovanović, I., Vianello, R. & Hranjec, M. (2021) Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential. Journal of molecular liquids, 342, 117527, 14 doi:10.1016/j.molliq.2021.117527.
@article{article, author = {Bo\v{c}ek, Ida and Star\v{c}evi\'{c}, Kristina and Novak Jovanovi\'{c}, Ivana and Vianello, Robert and Hranjec, Marijana}, year = {2021}, pages = {14}, DOI = {10.1016/j.molliq.2021.117527}, chapter = {117527}, keywords = {acrylonitriles, antioxidative potential, DFT calculations, electrochemical oxidation potential, imidazo[4, 5-b]pyridines, solvent effects}, journal = {Journal of molecular liquids}, doi = {10.1016/j.molliq.2021.117527}, volume = {342}, issn = {0167-7322}, title = {Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential}, keyword = {acrylonitriles, antioxidative potential, DFT calculations, electrochemical oxidation potential, imidazo[4, 5-b]pyridines, solvent effects}, chapternumber = {117527} }
@article{article, author = {Bo\v{c}ek, Ida and Star\v{c}evi\'{c}, Kristina and Novak Jovanovi\'{c}, Ivana and Vianello, Robert and Hranjec, Marijana}, year = {2021}, pages = {14}, DOI = {10.1016/j.molliq.2021.117527}, chapter = {117527}, keywords = {acrylonitriles, antioxidative potential, DFT calculations, electrochemical oxidation potential, imidazo[4, 5-b]pyridines, solvent effects}, journal = {Journal of molecular liquids}, doi = {10.1016/j.molliq.2021.117527}, volume = {342}, issn = {0167-7322}, title = {Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential}, keyword = {acrylonitriles, antioxidative potential, DFT calculations, electrochemical oxidation potential, imidazo[4, 5-b]pyridines, solvent effects}, chapternumber = {117527} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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  • CA Search (Chemical Abstracts)


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