Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid

New tetrahydropyrazino[2,3-c]quinolin-5(6H)-ones were prepared from 3-chloroquinoline-2,4(1H,3H)-diones and ethylene diamine. In their reaction with HNCO, an unprecedented molecular rearrangement produced new types of hydantoin derivatives. All prepared compounds were characterized on the basis of t...

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Autores principales: Klásek, Antonín, Lyčka, Antonín, Křemen, Filip, Růžička, Aleš, Rouchal, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9143794/
https://www.ncbi.nlm.nih.gov/pubmed/35628291
http://dx.doi.org/10.3390/ijms23105481
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author Klásek, Antonín
Lyčka, Antonín
Křemen, Filip
Růžička, Aleš
Rouchal, Michal
author_facet Klásek, Antonín
Lyčka, Antonín
Křemen, Filip
Růžička, Aleš
Rouchal, Michal
author_sort Klásek, Antonín
collection PubMed
description New tetrahydropyrazino[2,3-c]quinolin-5(6H)-ones were prepared from 3-chloroquinoline-2,4(1H,3H)-diones and ethylene diamine. In their reaction with HNCO, an unprecedented molecular rearrangement produced new types of hydantoin derivatives. All prepared compounds were characterized on the basis of their (1)H, (13)C, and (15)N NMR and ESI mass spectra and some were authenticated by X-ray analysis of single crystalline material. A proposed mechanism for rearrangement is discussed in this essay. The CDK and ABL inhibition activity as well as in vitro cytotoxicity of the prepared compounds was also tested.
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spelling pubmed-91437942022-05-29 Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid Klásek, Antonín Lyčka, Antonín Křemen, Filip Růžička, Aleš Rouchal, Michal Int J Mol Sci Article New tetrahydropyrazino[2,3-c]quinolin-5(6H)-ones were prepared from 3-chloroquinoline-2,4(1H,3H)-diones and ethylene diamine. In their reaction with HNCO, an unprecedented molecular rearrangement produced new types of hydantoin derivatives. All prepared compounds were characterized on the basis of their (1)H, (13)C, and (15)N NMR and ESI mass spectra and some were authenticated by X-ray analysis of single crystalline material. A proposed mechanism for rearrangement is discussed in this essay. The CDK and ABL inhibition activity as well as in vitro cytotoxicity of the prepared compounds was also tested. MDPI 2022-05-13 /pmc/articles/PMC9143794/ /pubmed/35628291 http://dx.doi.org/10.3390/ijms23105481 Text en © 2022 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
Klásek, Antonín
Lyčka, Antonín
Křemen, Filip
Růžička, Aleš
Rouchal, Michal
Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid
title Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid
title_full Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid
title_fullStr Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid
title_full_unstemmed Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid
title_short Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid
title_sort molecular rearrangement of pyrazino[2,3-c]quinolin-5(6h)-ones during their reaction with isocyanic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9143794/
https://www.ncbi.nlm.nih.gov/pubmed/35628291
http://dx.doi.org/10.3390/ijms23105481
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