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New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

The well-known aminoazoles, 3-amino-5-methylisoxazole and 5-amino-N-aryl-1H-pyrazole-4-carboxamides, were studied as an amine component in Ugi and Groebke–Blackburn–Bienaymé multicomponent reactions. The first example of an application of aminoazoles in an Ugi four-component reaction was discovered...

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Autores principales: Murlykina, Maryna V, Kornet, Maryna N, Desenko, Sergey M, Shishkina, Svetlana V, Shishkin, Oleg V, Brazhko, Aleksander A, Musatov, Vladimir I, Van der Eycken, Erik V, Chebanov, Valentin A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480327/
https://www.ncbi.nlm.nih.gov/pubmed/28684984
http://dx.doi.org/10.3762/bjoc.13.104
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author Murlykina, Maryna V
Kornet, Maryna N
Desenko, Sergey M
Shishkina, Svetlana V
Shishkin, Oleg V
Brazhko, Aleksander A
Musatov, Vladimir I
Van der Eycken, Erik V
Chebanov, Valentin A
author_facet Murlykina, Maryna V
Kornet, Maryna N
Desenko, Sergey M
Shishkina, Svetlana V
Shishkin, Oleg V
Brazhko, Aleksander A
Musatov, Vladimir I
Van der Eycken, Erik V
Chebanov, Valentin A
author_sort Murlykina, Maryna V
collection PubMed
description The well-known aminoazoles, 3-amino-5-methylisoxazole and 5-amino-N-aryl-1H-pyrazole-4-carboxamides, were studied as an amine component in Ugi and Groebke–Blackburn–Bienaymé multicomponent reactions. The first example of an application of aminoazoles in an Ugi four-component reaction was discovered and novel features of a Groebke–Blackburn–Bienaymé cyclocondensation are established and discussed. The heterocycles obtained were evaluated for their antibacterial activity and several of them demonstrated a weak antimicrobial effect, but for most of the compounds a 30–50% increase in biomass of Gram-positive strains (mainly B. subtilis) compared to control was observed.
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spelling pubmed-54803272017-07-06 New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized Murlykina, Maryna V Kornet, Maryna N Desenko, Sergey M Shishkina, Svetlana V Shishkin, Oleg V Brazhko, Aleksander A Musatov, Vladimir I Van der Eycken, Erik V Chebanov, Valentin A Beilstein J Org Chem Full Research Paper The well-known aminoazoles, 3-amino-5-methylisoxazole and 5-amino-N-aryl-1H-pyrazole-4-carboxamides, were studied as an amine component in Ugi and Groebke–Blackburn–Bienaymé multicomponent reactions. The first example of an application of aminoazoles in an Ugi four-component reaction was discovered and novel features of a Groebke–Blackburn–Bienaymé cyclocondensation are established and discussed. The heterocycles obtained were evaluated for their antibacterial activity and several of them demonstrated a weak antimicrobial effect, but for most of the compounds a 30–50% increase in biomass of Gram-positive strains (mainly B. subtilis) compared to control was observed. Beilstein-Institut 2017-05-31 /pmc/articles/PMC5480327/ /pubmed/28684984 http://dx.doi.org/10.3762/bjoc.13.104 Text en Copyright © 2017, Murlykina et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Murlykina, Maryna V
Kornet, Maryna N
Desenko, Sergey M
Shishkina, Svetlana V
Shishkin, Oleg V
Brazhko, Aleksander A
Musatov, Vladimir I
Van der Eycken, Erik V
Chebanov, Valentin A
New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
title New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
title_full New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
title_fullStr New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
title_full_unstemmed New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
title_short New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
title_sort new tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480327/
https://www.ncbi.nlm.nih.gov/pubmed/28684984
http://dx.doi.org/10.3762/bjoc.13.104
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