4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides
The article discusses effective methods for the synthesis of unsymmetrical disulfides, which are important in the development of new bioactive molecules, pharmaceuticals, and materials for bioconjugation and systemic release. The aim of the work is to develop a method for the synthesis of unsymme...
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| Format: | Article |
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Zaporizhzhia State Medical and Pharmaceutical University
2025-03-01
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| Series: | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
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| Online Access: | https://pharmed.zsmu.edu.ua/article/view/328770/323370 |
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| author | Yu. V. Karpenko M. O. Panasenko |
| author_facet | Yu. V. Karpenko M. O. Panasenko |
| author_sort | Yu. V. Karpenko |
| collection | DOAJ |
| description | The article discusses effective methods for the synthesis of unsymmetrical disulfides, which are important in the development of new bioactive molecules, pharmaceuticals, and materials for bioconjugation and systemic release.
The aim of the work is to develop a method for the synthesis of unsymmetrical disulfides of 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiols under mild conditions, with high selectivity and wide tolerance to functional groups, including the disulfide fragment as a promising structural framework for the development of new active pharmaceutical ingredients.
Materials and methods. 1H NMR spectra were recorded on a Bruker AC-500 spectrometer (500 MHz) in DMSO-d6. Elemental analysis (C, H, N, S) was performed using an ELEMENTAR vario EL cube. Melting points were determined using the capillary method.
Results. A new strategy for the synthesis of unsymmetrical disulfides of 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiols using 1-chlorobenzotriazole has been developed, providing high product yields and selective transformation. This method does not require low temperatures and demonstrates high compatibility with various functional groups, allowing easy modification of molecules and further research potential. Spectral data confirm the structure of the obtained compounds and indicate the formation of stable disulfide bonds.
Conclusions. The synthesis of new unsymmetrical disulfides of 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiols was successfully carried out under mild conditions using 1-chlorobenzotriazole as a selective reagent, resulting in high yields and good tolerance to functional groups. Their structural similarity to natural antioxidants such as cystine and allicin makes them promising model compounds for further studies of the mechanisms of redox activity and the development of new drugs to regulate oxidative stress. |
| format | Article |
| id | doaj-art-ae3ea65c79bf407f8d642624533f69af |
| institution | DOAJ |
| issn | 2306-8094 2409-2932 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Zaporizhzhia State Medical and Pharmaceutical University |
| record_format | Article |
| series | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| spelling | doaj-art-ae3ea65c79bf407f8d642624533f69af2025-08-20T03:11:36ZengZaporizhzhia State Medical and Pharmaceutical UniversityAktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki2306-80942409-29322025-03-01182123130https://doi.org/10.14739/2409-2932.2025.2.3287704-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfidesYu. V. Karpenko 0https://orcid.org/0000-0002-4390-9949M. O. Panasenko1https://orcid.org/0000-0002-2619-3846Zaporizhzhia State Medical and Pharmaceutical University, UkraineZaporizhzhia State Medical and Pharmaceutical University, UkraineThe article discusses effective methods for the synthesis of unsymmetrical disulfides, which are important in the development of new bioactive molecules, pharmaceuticals, and materials for bioconjugation and systemic release. The aim of the work is to develop a method for the synthesis of unsymmetrical disulfides of 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiols under mild conditions, with high selectivity and wide tolerance to functional groups, including the disulfide fragment as a promising structural framework for the development of new active pharmaceutical ingredients. Materials and methods. 1H NMR spectra were recorded on a Bruker AC-500 spectrometer (500 MHz) in DMSO-d6. Elemental analysis (C, H, N, S) was performed using an ELEMENTAR vario EL cube. Melting points were determined using the capillary method. Results. A new strategy for the synthesis of unsymmetrical disulfides of 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiols using 1-chlorobenzotriazole has been developed, providing high product yields and selective transformation. This method does not require low temperatures and demonstrates high compatibility with various functional groups, allowing easy modification of molecules and further research potential. Spectral data confirm the structure of the obtained compounds and indicate the formation of stable disulfide bonds. Conclusions. The synthesis of new unsymmetrical disulfides of 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiols was successfully carried out under mild conditions using 1-chlorobenzotriazole as a selective reagent, resulting in high yields and good tolerance to functional groups. Their structural similarity to natural antioxidants such as cystine and allicin makes them promising model compounds for further studies of the mechanisms of redox activity and the development of new drugs to regulate oxidative stress.https://pharmed.zsmu.edu.ua/article/view/328770/323370124-triazoledisulfidesmild conditionshigh selectivityantimicrobial activityantioxidant activity |
| spellingShingle | Yu. V. Karpenko M. O. Panasenko 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki 1 2 4-triazole disulfides mild conditions high selectivity antimicrobial activity antioxidant activity |
| title | 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides |
| title_full | 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides |
| title_fullStr | 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides |
| title_full_unstemmed | 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides |
| title_short | 4-phenyl-5-((pyrimidin-2-ylthio)methyl)-1,2,4-triazole-3-thiol as a platform for the synthesis of unsymmetrical disulfides |
| title_sort | 4 phenyl 5 pyrimidin 2 ylthio methyl 1 2 4 triazole 3 thiol as a platform for the synthesis of unsymmetrical disulfides |
| topic | 1 2 4-triazole disulfides mild conditions high selectivity antimicrobial activity antioxidant activity |
| url | https://pharmed.zsmu.edu.ua/article/view/328770/323370 |
| work_keys_str_mv | AT yuvkarpenko 4phenyl5pyrimidin2ylthiomethyl124triazole3thiolasaplatformforthesynthesisofunsymmetricaldisulfides AT mopanasenko 4phenyl5pyrimidin2ylthiomethyl124triazole3thiolasaplatformforthesynthesisofunsymmetricaldisulfides |