Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies
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2019
Authors
Jakovljević, KatarinaJoksović, Milan D.
Botta, Bruno
Jovanović, Ljiljana S.
Avdović, Edina
Marković, Zoran
Mihailović, Vladimir
Andrić, Marijana
Trifunović, Snežana S.
Marković, Violeta
Article (Published version)
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A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechan...ism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation.
Keywords:
1,3,4-thiadiazole / Antioxidant / DFT / Electrochemistry / Protocatechuic acidSource:
Comptes Rendus Chimie, 2019, 22, 8, 585-598Publisher:
- Elsevier
Funding / projects:
- Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-172016)
- Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-172014)
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-172015)
- Simultaneous Bioremediation and Soilification of Degraded Areas to Preserve Natural Resources of Biologically Active Substances, and Development and Production of Biomaterials and Dietetic Products (RS-43004)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3739
DOI: 10.1016/j.crci.2019.06.001
ISSN: 1631-0748
WoS: 000525392600005
Scopus: 2-s2.0-85068213922
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Jakovljević, Katarina AU - Joksović, Milan D. AU - Botta, Bruno AU - Jovanović, Ljiljana S. AU - Avdović, Edina AU - Marković, Zoran AU - Mihailović, Vladimir AU - Andrić, Marijana AU - Trifunović, Snežana S. AU - Marković, Violeta PY - 2019 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3738 AB - A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechanism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation. PB - Elsevier T2 - Comptes Rendus Chimie T1 - Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies VL - 22 IS - 8 SP - 585 EP - 598 DO - 10.1016/j.crci.2019.06.001 ER -
@article{ author = "Jakovljević, Katarina and Joksović, Milan D. and Botta, Bruno and Jovanović, Ljiljana S. and Avdović, Edina and Marković, Zoran and Mihailović, Vladimir and Andrić, Marijana and Trifunović, Snežana S. and Marković, Violeta", year = "2019", abstract = "A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechanism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation.", publisher = "Elsevier", journal = "Comptes Rendus Chimie", title = "Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies", volume = "22", number = "8", pages = "585-598", doi = "10.1016/j.crci.2019.06.001" }
Jakovljević, K., Joksović, M. D., Botta, B., Jovanović, L. S., Avdović, E., Marković, Z., Mihailović, V., Andrić, M., Trifunović, S. S.,& Marković, V.. (2019). Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies. in Comptes Rendus Chimie Elsevier., 22(8), 585-598. https://doi.org/10.1016/j.crci.2019.06.001
Jakovljević K, Joksović MD, Botta B, Jovanović LS, Avdović E, Marković Z, Mihailović V, Andrić M, Trifunović SS, Marković V. Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies. in Comptes Rendus Chimie. 2019;22(8):585-598. doi:10.1016/j.crci.2019.06.001 .
Jakovljević, Katarina, Joksović, Milan D., Botta, Bruno, Jovanović, Ljiljana S., Avdović, Edina, Marković, Zoran, Mihailović, Vladimir, Andrić, Marijana, Trifunović, Snežana S., Marković, Violeta, "Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies" in Comptes Rendus Chimie, 22, no. 8 (2019):585-598, https://doi.org/10.1016/j.crci.2019.06.001 . .