1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
1,3-Dithiocyanatoacetone was prepared by reaction of 1,3-dichloroacetone with potassium thiocyanate in ethanol in almost quantitative yield. In contrast to the NMR spectra recorded in acetone-d6, NMR spectra of 1,3-dithiocyanatoacetone in DMSO-d6 solution revealed the presence of the enol form. The...
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| Главные авторы: | , , , , , , , |
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| Формат: | Статья |
| Язык: | English |
| Опубликовано: |
Springer Science and Business Media B.V.
2024
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| Темы: | |
| Online-ссылка: | https://dspace.ncfu.ru/handle/123456789/29209 |
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| Краткое описание: | 1,3-Dithiocyanatoacetone was prepared by reaction of 1,3-dichloroacetone with potassium thiocyanate in ethanol in almost quantitative yield. In contrast to the NMR spectra recorded in acetone-d6, NMR spectra of 1,3-dithiocyanatoacetone in DMSO-d6 solution revealed the presence of the enol form. The keto-enol tautomerism is discussed and the structure of main conformers and tautomers of dithiocyanatoacetone and its acid hydrolysis product, S-[(2-oxo-2,3-dihydro- 1,3-thiazol-4-yl)methyl]thiocarbamate, was investigated by quantum chemical methods. The vibrational spectra were calculated and found to be in a good agreement with the experimental FT-IR spectra. The structure of 1,3-dithiocyanatoacetone and S-[(2-oxo-2,3-dihydro-1,3-thiazol-4-yl)methyl]thiocarbamate was studied by X-ray diffraction analysis. Molecular docking and bioavailability parameters calculations showed the potential of the compounds as carbonic anhydrase inhibitors. |
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