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New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity

The biologically active compound 3-aminopropylsilatrane (a compound with a pentacoordinated silicon atom) underwent an aza-Michael reaction with various acrylates and other Michael acceptors. Depending on the molar ratio, the reaction yielded Michael mono- or diadducts (11 examples) containing funct...

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Autores principales: Adamovich, Sergey N., Ushakov, Igor A., Oborina, Elizaveta N., Lukyanova, Svetlana V., Komarov, Vladislav Y.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10298438/
https://www.ncbi.nlm.nih.gov/pubmed/37373114
http://dx.doi.org/10.3390/ijms24129965
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author Adamovich, Sergey N.
Ushakov, Igor A.
Oborina, Elizaveta N.
Lukyanova, Svetlana V.
Komarov, Vladislav Y.
author_facet Adamovich, Sergey N.
Ushakov, Igor A.
Oborina, Elizaveta N.
Lukyanova, Svetlana V.
Komarov, Vladislav Y.
author_sort Adamovich, Sergey N.
collection PubMed
description The biologically active compound 3-aminopropylsilatrane (a compound with a pentacoordinated silicon atom) underwent an aza-Michael reaction with various acrylates and other Michael acceptors. Depending on the molar ratio, the reaction yielded Michael mono- or diadducts (11 examples) containing functional groups (silatranyl, carbonyl, nitrile, amino, etc.). These compounds were characterized via IR and NMR spectroscopy, mass spectrometry, X-ray diffraction, and elemental analysis. Calculations (using in silico, PASS, and SwissADMET online software) revealed that the functionalized (hybrid) silatranes were bioavailable, druglike compounds that exhibited pronounced antineoplastic and macrophage-colony-stimulating activity. The in vitro effect of silatranes on the growth of pathogenic bacteria (Listeria, Staphylococcus, and Yersinia) was studied. It was found that the synthesized compounds exerted inhibitory and stimulating effects in high and low concentrations, respectively.
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spelling pubmed-102984382023-06-28 New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity Adamovich, Sergey N. Ushakov, Igor A. Oborina, Elizaveta N. Lukyanova, Svetlana V. Komarov, Vladislav Y. Int J Mol Sci Article The biologically active compound 3-aminopropylsilatrane (a compound with a pentacoordinated silicon atom) underwent an aza-Michael reaction with various acrylates and other Michael acceptors. Depending on the molar ratio, the reaction yielded Michael mono- or diadducts (11 examples) containing functional groups (silatranyl, carbonyl, nitrile, amino, etc.). These compounds were characterized via IR and NMR spectroscopy, mass spectrometry, X-ray diffraction, and elemental analysis. Calculations (using in silico, PASS, and SwissADMET online software) revealed that the functionalized (hybrid) silatranes were bioavailable, druglike compounds that exhibited pronounced antineoplastic and macrophage-colony-stimulating activity. The in vitro effect of silatranes on the growth of pathogenic bacteria (Listeria, Staphylococcus, and Yersinia) was studied. It was found that the synthesized compounds exerted inhibitory and stimulating effects in high and low concentrations, respectively. MDPI 2023-06-09 /pmc/articles/PMC10298438/ /pubmed/37373114 http://dx.doi.org/10.3390/ijms24129965 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Adamovich, Sergey N.
Ushakov, Igor A.
Oborina, Elizaveta N.
Lukyanova, Svetlana V.
Komarov, Vladislav Y.
New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity
title New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity
title_full New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity
title_fullStr New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity
title_full_unstemmed New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity
title_short New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity
title_sort new 3-aminopropylsilatrane derivatives: synthesis, structure, properties, and biological activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10298438/
https://www.ncbi.nlm.nih.gov/pubmed/37373114
http://dx.doi.org/10.3390/ijms24129965
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