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:	Dotsenko, V. V., Доценко, В. В., Ovcharov, S. N., Овчаров, С. Н., Aksenov, N. A., Аксенов, Н. А., Aksenova, I. V., Аксенова, И. В.
Формат:	Статья
Язык:	English
Опубликовано:	Springer Science and Business Media B.V. 2024
Темы:	ADMET properties α-thiocyanato ketones DFT calculations Molecular docking Organic thiocyanates X-ray analysis
Online-ссылка:	https://dspace.ncfu.ru/handle/123456789/29209
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id	ir-123456789-29209
record_format	dspace
spelling	ir-123456789-292092024-11-08T09:16:22Z 1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies Dotsenko, V. V. Доценко, В. В. Ovcharov, S. N. Овчаров, С. Н. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. ADMET properties α-thiocyanato ketones DFT calculations Molecular docking Organic thiocyanates X-ray analysis 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. 2024-11-08T09:14:41Z 2024-11-08T09:14:41Z 2024 Статья Kindop V.K., Bespalov A.V., Dotsenko V.V., Temerdashev A.Z., Vasilin V.K., Jassim N.T., Netreba E.E., Ovcharov S.N., Aksenov N.A., Aksenova I.V. 1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies // Research on Chemical Intermediates. - 2024. - 50 (10). - pp. 5039 - 5060. - DOI: 10.1007/s11164-024-05375-6 https://dspace.ncfu.ru/handle/123456789/29209 en Research on Chemical Intermediates application/pdf application/pdf Springer Science and Business Media B.V.
institution	СКФУ
collection	Репозиторий
language	English
topic	ADMET properties α-thiocyanato ketones DFT calculations Molecular docking Organic thiocyanates X-ray analysis
spellingShingle	ADMET properties α-thiocyanato ketones DFT calculations Molecular docking Organic thiocyanates X-ray analysis Dotsenko, V. V. Доценко, В. В. Ovcharov, S. N. Овчаров, С. Н. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. 1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
description	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.
format	Статья
author	Dotsenko, V. V. Доценко, В. В. Ovcharov, S. N. Овчаров, С. Н. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_facet	Dotsenko, V. V. Доценко, В. В. Ovcharov, S. N. Овчаров, С. Н. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_sort	Dotsenko, V. V.
title	1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
title_short	1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
title_full	1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
title_fullStr	1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
title_full_unstemmed	1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
title_sort	1,3-dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies
publisher	Springer Science and Business Media B.V.
publishDate	2024
url	https://dspace.ncfu.ru/handle/123456789/29209
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1,3-Dithiocyanatoacetone: improved synthesis, detailed structural studies and in silico docking studies

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