Evaluation of Antioxidant Activity of 1, 2, 4-Triazole Derivatives With Morpholine Moiety
Yıl 2022,
, 73 - 82, 01.06.2022
Roman Shcherbyna
,
Yevhen Pruhlo
Maryna Duchenko
,
Mariia Kulagina
Victoriia Kudria
Vashchuk Valentyna
Öz
The aim of the work was to study the antioxidant activity of 4-R-3- (morpholinomethyl)-4H-1,2,4-triazole-5-thioles and their alkyl derivatives in vitro using the method of non-enzymatic initiation of lipid peroxidation. Among the 45 compounds studied, 8 showed varying degrees of AOA. The most pronounced AOA has 4-amino-3-(morpholinomethyl)-4H-1,2,4-triazole-5-thiol. It was found that in most cases the introduction in alkyl-derivatives of 4-R-3-(morpholinomethyl)-4H-1,2,4-triazole-5-thioles free amino group or phenyl substituent to the N4 atom of the 1,2,4-triazole nucleus, accompanied with increasing of AOA for test substances. In almost all cases, the presence on the N4 atom of 1,2,4-triazole nucleus methyl or ethyl groups has the opposite effect, even in comparison with control groups.
Destekleyen Kurum
The Ministry of Education and Science of Ukraine
Proje Numarası
0120U101649
Teşekkür
The authors are highly thankful to the The Ministry of Education and Science of Ukraine for financial support which was given according to scientific topic № 0120U101649 "Synthesis, modification and study of the properties of 1,2,4-triazole derivatives for the purpose of antimicrobial drug production".
Kaynakça
- 1. Halliwell, B: Antioxidants in human health and disease. Annual review of nutrition 1996, 16(1): 33-50.
- 2. Reische, DW, Lillard, DA, Eitenmiller, RR: Antioxidants. Food lipids: chemistry, nutrition, and biotechnology (Ed. 2): The Dannon Company; Fort Worth, Texas, USA, 2002.
- 3. Sies, H, Berndt, C, Jones, DP: Oxidative stress. Annual review of biochemistry 2017, 86: 715-748.
- 4. Ihnatova, T, Kaplaushenko, A, Frolova, Y, Pryhlo, E: Synthesis and antioxidant properties of some new 5-phenethyl-3-thio-1,2,4-triazoles. Pharmacia 2021, 68(1): 129–133. https://doi.org/10.3897/pharmacia.68.e53320
- 5. Gotsulya, A: Synthesis and antioxidant activities of alkylderivatives of 5-(5-methyl-1H-pyrazol-3-yl)-4-phenyl-4H-1,2,4-triazole-3-thiole. Ankara Universitesi Eczacilik Fakultesi Dergisi 2020, 44(2): 211–219. https://doi.org/10.33483/jfpau.616116
- 6. Hulina, YS, Kaplaushenko, AG: Synthesis, physical and chemical properties of 5-((1H-tetrazole-1-yl) methyl)-4-R-4H-1,2,4-triazole-3-thiols and their chemical transformations. Biopharmaceutical journal 2018, 10(1): 26-30.
- 7. Sameliuk, Y, Kaplaushenko, T, Al Zedan, F: 1,2,4-Triazole derivatives in medicine and pharmacy and application prospects. Ankara Universitesi Eczacilik Fakultesi Dergisi 2021, 598–614. https://doi.org/10.33483/jfpau.885888
- 8. Safonov, A: Derivatives of 3-(alkylthio)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-4-amines as increasing efficiency substances. Indonesian journal of pharmacy 2018, 29(3): 167-172. https://doi.org/10.14499/indonesianjpharm29iss3pp167
- 9. Karpun, Y; Polishchuk, N: Synthesis and antimicrobial activity of s-substituted derivatives of 1,2,4-triazol-3-thiol. ScienceRise: Pharmaceutical Science, 2021, 3(31): 64–69. https://doi.org/10.15587/2519-4852.2021.235976
- 10. Frolova, Y, Kaplaushenko, A, Nagornaya, N: Design, synthesis, antimicrobial and antifungal activities of new 1, 2, 4-triazole derivatives containing 1h-tetrazole moiety. Journal of Faculty of Pharmacy of Ankara University 2020, 44(1): 70-88.
- 11. Samelyuk, YG, Kaplaushenko, AG: Synthesis of 3-alkylthio(sulfo)-1,2,4-triazoles, Containing methoxyphenyl substituents at C5 atoms, Their antipyretic activity, Propensity to adsorption and acute toxicity. Journal of Chemical and Pharmaceutical Research 2014, 6(5): 1117-1121.
- 12. Shcherbyna, R, Vashchyk, Y: The research of 1,2,4-triazole derivatives hepatoprotective activity under tetracycline and infectious hepatitis. Journal of Faculty of Pharmacy of Ankara University 2019, 43 (2): 135-146 . DOI: 10.33483/jfpau.487173
- 13. Shcherbyna, R: An investigation of the pharmacokinetics and potential metabolites of potassium 2-((4-amino-5-(morfolinometyl)-4H-1,2,4-triazol-3-yl)thio)acetate on rats. Journal of Faculty of Pharmacy of Ankara University 2020, 44 (2): 233-241. DOI: 10.33483/jfpau.681611
- 14. Vashchyk, Y, Shcherbyna, R, Parchenko, V, Bushueva, İ, Gutyj, B, Fotına, H, Fotına, T, Stronsky, Y: Histological study of a corrective influence of a compound potassium 2-((4-amino-5-(morpholinomethyl)-4H-1,2,4-triazol-3-yl)thio)acetate (PKR-173) on the state of chicken's liver under infection by pseudomonas aeruginosa. Journal of Faculty of Pharmacy of Ankara University 2020, 44 (1): 1-17. DOI: 10.33483/jfpau.567757
- 15. Shcherbyna, R, Parchenko, V, Martynyshyn, V, Hunchak, V: Evaluation of acute and subacute toxicity of oil liniment based on 4-((5-(decylthio)-4-methyl-4H-1,2,4- triazol-3-yl)methyl)morpholine . Journal of Faculty of Pharmacy of Ankara University 2018, 42 (1): 43-52. https://dergipark.org.tr/en/pub/jfpanu/issue/42653/514314
- 16. Safonov, A: Microwave synthesis of new N-R-3-(alkylthio)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-4-amines. Ankara Universitesi Eczacilik Fakultesi Dergisi 2020, 44 (1): 89–98. https://doi.org/10.33483/jfpau.620599
- 17. Safonov, A, Nevmyvaka, A, Panasenko, O, Knysh, Y: Microwave synthesis of 3- and 4-substituted-5-((3-phenylpropyl)thio)-4H-1,2,4-triazoles. Ankara Universitesi Eczacilik Fakultesi Dergisi 2021, 45 (3):457–466. https://doi.org/10.33483/jfpau.902274
- 18. Shcherbyna, R: Microwave-assisted synthesis of some new derivatives of 4-substituted-3-(morpholinomethyl)-4H-1,2,4-triazole-5-thioles . Journal of Faculty of Pharmacy of Ankara University 2019, 43 (3): 220-229. DOI: 10.33483/jfpau.533166
- 19. Safonov, A: Method of synthesis novel N’-substituted- 2-((5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides. Ankara Universitesi Eczacilik Fakultesi Dergisi 2020, 44 (2): 242–252. https://doi.org/10.33483/jfpau.580011
- 20. Karpun, Y: Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. Hacettepe University Journal of the Faculty of Pharmacy, 2021, 41(3): 150-161. doi:10.52794/hujpharm.973420
- 21. Shcherbyna, RO:The synthesis and prediction of biological activity in silico for new alkyl derivatives of 4-R-3-(morfolinometylen)-4H-1,2,4-triazole-5-thioles.Ukrainian biopharmaceutical journal 2016, 3 (44): 34-38.
- 22. Gubsky YuI, Duna, VV: Methods For Evaluating The Antioxidant Properties Of Physiologically Active Compounds In The Initiation Of Free Radical Processes In In Vitro Experiments: A Method. Rivers: DFC of the Ministry of Health of Ukraine, Kyiev, Ukraine, 2002.
- 23. Klebanov GI, Babenkova IV, Teselkin Yu.O.: Evaluation Of Antioxidant Activity Of Blood Plasma With The Use Of Yolk Lipoproteins -Lab. Case: Moskow, USSR,1988.
- 24. Hilbe, JM: STATISTICA 7: An overview. The American Statistician 2007, 61(1): 91-94.
- 25. Rebrova, OYu: Statistical analysis of medical data. Application of the STATISTICA application package; MediaSfera, Moscow, Russian Federation, 2002.
Yıl 2022,
, 73 - 82, 01.06.2022
Roman Shcherbyna
,
Yevhen Pruhlo
Maryna Duchenko
,
Mariia Kulagina
Victoriia Kudria
Vashchuk Valentyna
Proje Numarası
0120U101649
Kaynakça
- 1. Halliwell, B: Antioxidants in human health and disease. Annual review of nutrition 1996, 16(1): 33-50.
- 2. Reische, DW, Lillard, DA, Eitenmiller, RR: Antioxidants. Food lipids: chemistry, nutrition, and biotechnology (Ed. 2): The Dannon Company; Fort Worth, Texas, USA, 2002.
- 3. Sies, H, Berndt, C, Jones, DP: Oxidative stress. Annual review of biochemistry 2017, 86: 715-748.
- 4. Ihnatova, T, Kaplaushenko, A, Frolova, Y, Pryhlo, E: Synthesis and antioxidant properties of some new 5-phenethyl-3-thio-1,2,4-triazoles. Pharmacia 2021, 68(1): 129–133. https://doi.org/10.3897/pharmacia.68.e53320
- 5. Gotsulya, A: Synthesis and antioxidant activities of alkylderivatives of 5-(5-methyl-1H-pyrazol-3-yl)-4-phenyl-4H-1,2,4-triazole-3-thiole. Ankara Universitesi Eczacilik Fakultesi Dergisi 2020, 44(2): 211–219. https://doi.org/10.33483/jfpau.616116
- 6. Hulina, YS, Kaplaushenko, AG: Synthesis, physical and chemical properties of 5-((1H-tetrazole-1-yl) methyl)-4-R-4H-1,2,4-triazole-3-thiols and their chemical transformations. Biopharmaceutical journal 2018, 10(1): 26-30.
- 7. Sameliuk, Y, Kaplaushenko, T, Al Zedan, F: 1,2,4-Triazole derivatives in medicine and pharmacy and application prospects. Ankara Universitesi Eczacilik Fakultesi Dergisi 2021, 598–614. https://doi.org/10.33483/jfpau.885888
- 8. Safonov, A: Derivatives of 3-(alkylthio)-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-4-amines as increasing efficiency substances. Indonesian journal of pharmacy 2018, 29(3): 167-172. https://doi.org/10.14499/indonesianjpharm29iss3pp167
- 9. Karpun, Y; Polishchuk, N: Synthesis and antimicrobial activity of s-substituted derivatives of 1,2,4-triazol-3-thiol. ScienceRise: Pharmaceutical Science, 2021, 3(31): 64–69. https://doi.org/10.15587/2519-4852.2021.235976
- 10. Frolova, Y, Kaplaushenko, A, Nagornaya, N: Design, synthesis, antimicrobial and antifungal activities of new 1, 2, 4-triazole derivatives containing 1h-tetrazole moiety. Journal of Faculty of Pharmacy of Ankara University 2020, 44(1): 70-88.
- 11. Samelyuk, YG, Kaplaushenko, AG: Synthesis of 3-alkylthio(sulfo)-1,2,4-triazoles, Containing methoxyphenyl substituents at C5 atoms, Their antipyretic activity, Propensity to adsorption and acute toxicity. Journal of Chemical and Pharmaceutical Research 2014, 6(5): 1117-1121.
- 12. Shcherbyna, R, Vashchyk, Y: The research of 1,2,4-triazole derivatives hepatoprotective activity under tetracycline and infectious hepatitis. Journal of Faculty of Pharmacy of Ankara University 2019, 43 (2): 135-146 . DOI: 10.33483/jfpau.487173
- 13. Shcherbyna, R: An investigation of the pharmacokinetics and potential metabolites of potassium 2-((4-amino-5-(morfolinometyl)-4H-1,2,4-triazol-3-yl)thio)acetate on rats. Journal of Faculty of Pharmacy of Ankara University 2020, 44 (2): 233-241. DOI: 10.33483/jfpau.681611
- 14. Vashchyk, Y, Shcherbyna, R, Parchenko, V, Bushueva, İ, Gutyj, B, Fotına, H, Fotına, T, Stronsky, Y: Histological study of a corrective influence of a compound potassium 2-((4-amino-5-(morpholinomethyl)-4H-1,2,4-triazol-3-yl)thio)acetate (PKR-173) on the state of chicken's liver under infection by pseudomonas aeruginosa. Journal of Faculty of Pharmacy of Ankara University 2020, 44 (1): 1-17. DOI: 10.33483/jfpau.567757
- 15. Shcherbyna, R, Parchenko, V, Martynyshyn, V, Hunchak, V: Evaluation of acute and subacute toxicity of oil liniment based on 4-((5-(decylthio)-4-methyl-4H-1,2,4- triazol-3-yl)methyl)morpholine . Journal of Faculty of Pharmacy of Ankara University 2018, 42 (1): 43-52. https://dergipark.org.tr/en/pub/jfpanu/issue/42653/514314
- 16. Safonov, A: Microwave synthesis of new N-R-3-(alkylthio)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-4-amines. Ankara Universitesi Eczacilik Fakultesi Dergisi 2020, 44 (1): 89–98. https://doi.org/10.33483/jfpau.620599
- 17. Safonov, A, Nevmyvaka, A, Panasenko, O, Knysh, Y: Microwave synthesis of 3- and 4-substituted-5-((3-phenylpropyl)thio)-4H-1,2,4-triazoles. Ankara Universitesi Eczacilik Fakultesi Dergisi 2021, 45 (3):457–466. https://doi.org/10.33483/jfpau.902274
- 18. Shcherbyna, R: Microwave-assisted synthesis of some new derivatives of 4-substituted-3-(morpholinomethyl)-4H-1,2,4-triazole-5-thioles . Journal of Faculty of Pharmacy of Ankara University 2019, 43 (3): 220-229. DOI: 10.33483/jfpau.533166
- 19. Safonov, A: Method of synthesis novel N’-substituted- 2-((5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides. Ankara Universitesi Eczacilik Fakultesi Dergisi 2020, 44 (2): 242–252. https://doi.org/10.33483/jfpau.580011
- 20. Karpun, Y: Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. Hacettepe University Journal of the Faculty of Pharmacy, 2021, 41(3): 150-161. doi:10.52794/hujpharm.973420
- 21. Shcherbyna, RO:The synthesis and prediction of biological activity in silico for new alkyl derivatives of 4-R-3-(morfolinometylen)-4H-1,2,4-triazole-5-thioles.Ukrainian biopharmaceutical journal 2016, 3 (44): 34-38.
- 22. Gubsky YuI, Duna, VV: Methods For Evaluating The Antioxidant Properties Of Physiologically Active Compounds In The Initiation Of Free Radical Processes In In Vitro Experiments: A Method. Rivers: DFC of the Ministry of Health of Ukraine, Kyiev, Ukraine, 2002.
- 23. Klebanov GI, Babenkova IV, Teselkin Yu.O.: Evaluation Of Antioxidant Activity Of Blood Plasma With The Use Of Yolk Lipoproteins -Lab. Case: Moskow, USSR,1988.
- 24. Hilbe, JM: STATISTICA 7: An overview. The American Statistician 2007, 61(1): 91-94.
- 25. Rebrova, OYu: Statistical analysis of medical data. Application of the STATISTICA application package; MediaSfera, Moscow, Russian Federation, 2002.