TY  - 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 . .

TY  - DATA
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/123456789/3739
PB  - Elsevier
T2  - Comptes Rendus Chimie
T1  - Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3739
ER  - 

@misc{
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",
publisher = "Elsevier",
journal = "Comptes Rendus Chimie",
title = "Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3739"
}

Jakovljević, K., Joksović, M. D., Botta, B., Jovanović, L. S., Avdović, E., Marković, Z., Mihailović, V., Andrić, M., Trifunović, S. S.,& Marković, V.. (2019). Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001. in Comptes Rendus Chimie
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_3739

Jakovljević K, Joksović MD, Botta B, Jovanović LS, Avdović E, Marković Z, Mihailović V, Andrić M, Trifunović SS, Marković V. Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001. in Comptes Rendus Chimie. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3739 .

Jakovljević, Katarina, Joksović, Milan D., Botta, Bruno, Jovanović, Ljiljana S., Avdović, Edina, Marković, Zoran, Mihailović, Vladimir, Andrić, Marijana, Trifunović, Snežana S., Marković, Violeta, "Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001" in Comptes Rendus Chimie (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3739 .