Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines
The reaction of pyrazolo[1,5-a]pyrazine-4(5H)ones with phosphorus tribromoxide in boiling benzene yielded 4-bromopyrazolo[1,5-a]pyrazines, and the thionation with phosphorus pentasulfide in pyridine at 90 °C led to pyrazolo[1,5-a]pyrazine-4(5H)thiones. The synthesized bromine derivatives are electro...
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| Дата: | 2019 |
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| Автори: | , , , , , , , |
| Формат: | Стаття |
| Мова: | English |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2019
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| Онлайн доступ: | https://ucj.org.ua/index.php/journal/article/view/22 |
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| Назва журналу: | Ukrainian Chemistry Journal |
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oai:ojs2.1444248.nisspano.web.hosting-test.net:article-222019-04-19T09:19:07Z Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines Hrynyshyn, Yevhenii Musiichuk, Hanna Komarovska-Porokhnyavets, Olena Is’kiv, Oksana Moskalenko, Nataliia Stasevych, Maryna Tsyzoryk, Nazar Vovk, Mykhailo 4-bromopyrazolo[1,5-a]pyrazines, pyrazolo[1,5-a]pyrazin-4(5H) thiones, thiophenoles, functionalized bromoalkanes, 4-aryl(alkyl)thio derivatives of pyrazolo[1,5-a]pyrazines, antibacterial and antifungal activity. The reaction of pyrazolo[1,5-a]pyrazine-4(5H)ones with phosphorus tribromoxide in boiling benzene yielded 4-bromopyrazolo[1,5-a]pyrazines, and the thionation with phosphorus pentasulfide in pyridine at 90 °C led to pyrazolo[1,5-a]pyrazine-4(5H)thiones. The synthesized bromine derivatives are electrophilic, and thiones are nucleophilic substrates. Their subsequent structural modification in the first case was carried out by interaction with thiophenols, and in the second case was conducted with functional halogenoalkanes. It was shown that bromides react with substituted thiophenols in dimethylformamide in the presence of potassium carbonate at 90 °C to form 4-arylthiopyrazolo[1,5-a]pyrazines with yields of 65–83 %. 4-S-methyl-functionalized derivatives of pyrazole[1,5-a]pyrazines with yields of 60–78 % were easily obtained by the alkylation of pyrazole[1,5-a]pyrazin-4(5H)thiones with a-bromoketones, bromoacetic acid, ethyl bromoacetate and bromoacetonitrile in the K2CO3—DMF system at room temperature. The composition of all synthesized compounds is in agreement with the results of elemental analysis and mass spectra. Their structure is confirmed by NMR 1H and 13C spectra. In particular, in the NMR 1H spectra of 4-arylthiopyrazolo[1,5-a]pyrazines, in addition to the characteristic signals of the pyrazole and pyrazine nuclei, signals of protons of thioaryl substituents are present in the range of 7.04 –8.05 ppm, and in NMR spectra of the 1H 4-S-methylfunctionalized derivatives of pyrazole[1,5-a]pyrazines signals of exocyclic methylene protons are present at 4.11– 5.02 ppm. Promising derivatives with antibacterial activity against the test cultures S. aureus (MIC = 7.8 g/mL), M. luteum (MIC = 3.9 g/mL), and antifungal activity against the test culture of fungus A. niger (MIC = 7.8 g/mL) were determined among 4-S-substituted pyrazole[1,5-a]pyrazines as a result of studies of the antimicrobial activity. V.I.Vernadsky Institute of General and Inorganic Chemistry 2019-02-15 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/22 10.33609/0041-6045.85.1.2019.58-66 Ukrainian Chemistry Journal; Vol. 85 No. 1 (2019): Ukrainian Chemistry Journal; 58-66 Украинский химический журнал; Том 85 № 1 (2019): Украинский химический журнал; 58-66 Український хімічний журнал; Том 85 № 1 (2019): Український хімічний журнал; 58-66 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/22/10 |
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Ukrainian Chemistry Journal |
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| datestamp_date |
2019-04-19T09:19:07Z |
| collection |
OJS |
| language |
English |
| topic_facet |
4-bromopyrazolo[1,5-a]pyrazines pyrazolo[1,5-a]pyrazin-4(5H) thiones thiophenoles functionalized bromoalkanes 4-aryl(alkyl)thio derivatives of pyrazolo[1,5-a]pyrazines antibacterial and antifungal activity. |
| format |
Article |
| author |
Hrynyshyn, Yevhenii Musiichuk, Hanna Komarovska-Porokhnyavets, Olena Is’kiv, Oksana Moskalenko, Nataliia Stasevych, Maryna Tsyzoryk, Nazar Vovk, Mykhailo |
| spellingShingle |
Hrynyshyn, Yevhenii Musiichuk, Hanna Komarovska-Porokhnyavets, Olena Is’kiv, Oksana Moskalenko, Nataliia Stasevych, Maryna Tsyzoryk, Nazar Vovk, Mykhailo Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines |
| author_facet |
Hrynyshyn, Yevhenii Musiichuk, Hanna Komarovska-Porokhnyavets, Olena Is’kiv, Oksana Moskalenko, Nataliia Stasevych, Maryna Tsyzoryk, Nazar Vovk, Mykhailo |
| author_sort |
Hrynyshyn, Yevhenii |
| title |
Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines |
| title_short |
Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines |
| title_full |
Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines |
| title_fullStr |
Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines |
| title_full_unstemmed |
Synthesis and Antimicrobial Activity of 4-Arylthio- and 4 Alkylthiofunctionalized Pyrazolo[1,5-a]pyrazines |
| title_sort |
synthesis and antimicrobial activity of 4-arylthio- and 4 alkylthiofunctionalized pyrazolo[1,5-a]pyrazines |
| description |
The reaction of pyrazolo[1,5-a]pyrazine-4(5H)ones with phosphorus tribromoxide in boiling benzene yielded 4-bromopyrazolo[1,5-a]pyrazines, and the thionation with phosphorus pentasulfide in pyridine at 90 °C led to pyrazolo[1,5-a]pyrazine-4(5H)thiones. The synthesized bromine derivatives are electrophilic, and thiones are nucleophilic substrates. Their subsequent structural modification in the first case was carried out by interaction with thiophenols, and in the second case was conducted with functional halogenoalkanes. It was shown that bromides react with substituted thiophenols in dimethylformamide in the presence of potassium carbonate at 90 °C to form 4-arylthiopyrazolo[1,5-a]pyrazines with yields of 65–83 %. 4-S-methyl-functionalized derivatives of pyrazole[1,5-a]pyrazines with yields of 60–78 % were easily obtained by the alkylation of pyrazole[1,5-a]pyrazin-4(5H)thiones with a-bromoketones, bromoacetic acid, ethyl bromoacetate and bromoacetonitrile in the K2CO3—DMF system at room temperature. The composition of all synthesized compounds is in agreement with the results of elemental analysis and mass spectra. Their structure is confirmed by NMR 1H and 13C spectra. In particular, in the NMR 1H spectra of 4-arylthiopyrazolo[1,5-a]pyrazines, in addition to the characteristic signals of the pyrazole and pyrazine nuclei, signals of protons of thioaryl substituents are present in the range of 7.04 –8.05 ppm, and in NMR spectra of the 1H 4-S-methylfunctionalized derivatives of pyrazole[1,5-a]pyrazines signals of exocyclic methylene protons are present at 4.11– 5.02 ppm. Promising derivatives with antibacterial activity against the test cultures S. aureus (MIC = 7.8 g/mL), M. luteum (MIC = 3.9 g/mL), and antifungal activity against the test culture of fungus A. niger (MIC = 7.8 g/mL) were determined among 4-S-substituted pyrazole[1,5-a]pyrazines as a result of studies of the antimicrobial activity. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2019 |
| url |
https://ucj.org.ua/index.php/journal/article/view/22 |
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2025-09-24T17:43:27Z |
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2025-09-24T17:43:27Z |
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