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New Reaction Products of Acetylacetone with Semicarbazide Derivatives

[Image: see text] A new approach is suggested herein for the synthesis of pyrazole derivatives by reacting 4-nitrosemicarbazide with acetylacetone. Additional studies were done on the reaction of acetylacetone with semicarbazide and its derivatives (4-aminosemicarbazide, methylsemicarbazide, and dim...

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Autores principales: Glukhacheva, Vera S., Il’yasov, Sergey G., Kazantsev, Igor V., Shestakova, Elena O., Il’yasov, Dmitri S., Eltsov, Ilia V., Nefedov, Andrey A., Gatilov, Yuri V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8015095/
https://www.ncbi.nlm.nih.gov/pubmed/33817525
http://dx.doi.org/10.1021/acsomega.1c00518
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author Glukhacheva, Vera S.
Il’yasov, Sergey G.
Kazantsev, Igor V.
Shestakova, Elena O.
Il’yasov, Dmitri S.
Eltsov, Ilia V.
Nefedov, Andrey A.
Gatilov, Yuri V.
author_facet Glukhacheva, Vera S.
Il’yasov, Sergey G.
Kazantsev, Igor V.
Shestakova, Elena O.
Il’yasov, Dmitri S.
Eltsov, Ilia V.
Nefedov, Andrey A.
Gatilov, Yuri V.
author_sort Glukhacheva, Vera S.
collection PubMed
description [Image: see text] A new approach is suggested herein for the synthesis of pyrazole derivatives by reacting 4-nitrosemicarbazide with acetylacetone. Additional studies were done on the reaction of acetylacetone with semicarbazide and its derivatives (4-aminosemicarbazide, methylsemicarbazide, and dimethylsemicarbazide). The study on the reaction with acetylacetone resulted in monocyclic 3,5-dimethyl-N-nitropyrazole-1-carboxamide, monocyclic 5-hydroxy-3,5-dimethyl-2-pyrazoline, and bicyclic bis(3,5-dimethylpyrazole-1-carbonyl)hydrazine, and conditions for the formation of acetone semicarbazone were identified. The structures of the resultant compounds were validated by physicochemical analytical methods, including X-ray diffraction. The computer-aided screening in the PASS prediction software discovered a high biological activity of the newly obtained compounds.
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spelling pubmed-80150952021-04-02 New Reaction Products of Acetylacetone with Semicarbazide Derivatives Glukhacheva, Vera S. Il’yasov, Sergey G. Kazantsev, Igor V. Shestakova, Elena O. Il’yasov, Dmitri S. Eltsov, Ilia V. Nefedov, Andrey A. Gatilov, Yuri V. ACS Omega [Image: see text] A new approach is suggested herein for the synthesis of pyrazole derivatives by reacting 4-nitrosemicarbazide with acetylacetone. Additional studies were done on the reaction of acetylacetone with semicarbazide and its derivatives (4-aminosemicarbazide, methylsemicarbazide, and dimethylsemicarbazide). The study on the reaction with acetylacetone resulted in monocyclic 3,5-dimethyl-N-nitropyrazole-1-carboxamide, monocyclic 5-hydroxy-3,5-dimethyl-2-pyrazoline, and bicyclic bis(3,5-dimethylpyrazole-1-carbonyl)hydrazine, and conditions for the formation of acetone semicarbazone were identified. The structures of the resultant compounds were validated by physicochemical analytical methods, including X-ray diffraction. The computer-aided screening in the PASS prediction software discovered a high biological activity of the newly obtained compounds. American Chemical Society 2021-03-17 /pmc/articles/PMC8015095/ /pubmed/33817525 http://dx.doi.org/10.1021/acsomega.1c00518 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Glukhacheva, Vera S.
Il’yasov, Sergey G.
Kazantsev, Igor V.
Shestakova, Elena O.
Il’yasov, Dmitri S.
Eltsov, Ilia V.
Nefedov, Andrey A.
Gatilov, Yuri V.
New Reaction Products of Acetylacetone with Semicarbazide Derivatives
title New Reaction Products of Acetylacetone with Semicarbazide Derivatives
title_full New Reaction Products of Acetylacetone with Semicarbazide Derivatives
title_fullStr New Reaction Products of Acetylacetone with Semicarbazide Derivatives
title_full_unstemmed New Reaction Products of Acetylacetone with Semicarbazide Derivatives
title_short New Reaction Products of Acetylacetone with Semicarbazide Derivatives
title_sort new reaction products of acetylacetone with semicarbazide derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8015095/
https://www.ncbi.nlm.nih.gov/pubmed/33817525
http://dx.doi.org/10.1021/acsomega.1c00518
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