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

dc.title	Molecular rearrangement of pyrazino[2,3‐c]quinolin‐5(6H)‐ones during their reaction with isocyanic acid	en
dc.contributor.author	Klásek, Antonín
dc.contributor.author	Lyčka, Antonín
dc.contributor.author	Křemen, Filip
dc.contributor.author	Růžička, Aleš
dc.contributor.author	Rouchal, Michal
dc.relation.ispartof	International Journal of Molecular Sciences
dc.identifier.issn	1661-6596 Scopus Sources, Sherpa/RoMEO, JCR
dc.identifier.issn	1422-0067 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued	2022-05-13
utb.relation.volume	23
utb.relation.issue	10
dc.citation.spage	5481
dc.type	article
dc.language.iso	en
dc.publisher	MDPI
dc.identifier.doi	10.3390/ijms23105481
dc.relation.uri	https://www.mdpi.com/1422-0067/23/10/5481
dc.subject	3-(3-acylureido)-2,3-dihydro-1H-indol-2-ones	en
dc.subject	4-alkylidene-1’H-spiro[imidazolidine-5,3’-indole]-2,2’-diones	en
dc.subject	imidazo[1,5-c]quinazoline-3,5-diones	en
dc.subject	1H-, 13C- and 15N-NMR	en
dc.subject	scXRD	en
dc.subject	biological activity	en
dc.description.abstract	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 H-1, C-13, and N-15 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.	en
utb.faculty	Faculty of Technology
dc.identifier.uri	http://hdl.handle.net/10563/1010983
utb.identifier.obdid	43883908
utb.identifier.scopus	2-s2.0-85129796244
utb.identifier.wok	000801936900001
utb.identifier.pubmed	35628291
utb.source	j-scopus
dc.date.accessioned	2022-05-24T21:47:33Z
dc.date.available	2022-05-24T21:47:33Z
dc.description.sponsorship	IGA/FT/2020/007
dc.description.sponsorship	Internal Funding Agency of Tomas Bata University in Zlin [IGA/FT/2020/007]
dc.rights	Attribution 4.0 International
dc.rights.uri	https://creativecommons.org/licenses/by/4.0/
dc.rights.access	openAccess
utb.ou	Department of Chemistry
utb.contributor.internalauthor	Klásek, Antonín
utb.contributor.internalauthor	Křemen, Filip
utb.contributor.internalauthor	Rouchal, Michal
utb.fulltext.affiliation	Antonín Klásek 1, Antonín Lyčka 2, Filip Křemen 1, Aleš Růžička 3 and Michal Rouchal 1,* 1 Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 5669, 760 01 Zlín, Czech Republic; klasek@utb.cz (A.K.); kremen.filip@seznam.cz (F.K.) 2 Department of Chemistry, Faculty of Science, University of Hradec Králové, Rokitanského 62, 530 03 Hradec Králové, Czech Republic; antonin.lycka@vuos.com 3 Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic; ales.ruzicka@upce.cz * Correspondence: rouchal@utb.cz; Tel.: +420-57-603-1432
utb.fulltext.dates	Received: 13 April 2022 Accepted: 12 May 2022 Published: 13 May 2022
utb.fulltext.sponsorship	This research was funded by the Internal Funding Agency of Tomas Bata University in Zlín (IGA/FT/2020/007).
utb.wos.affiliation	[Klasek, Antonin; Kremen, Filip; Rouchal, Michal] Tomas Bata Univ Zlin, Fac Technol, Dept Chem, Vavreckova 5669, Zlin 76001, Czech Republic; [Lycka, Antonin] Univ Hradec Kralove, Fac Sci, Dept Chem, Rokitanskeho 62, Hradec Kralove 53003, Czech Republic; [Ruzicka, Ales] Univ Pardubice, Fac Chem Technol, Dept Gen & Inorgan Chem, Studentska 573, Pardubice 53210, Czech Republic
utb.scopus.affiliation	Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 5669, Zlín, 760 01, Czech Republic; Department of Chemistry, Faculty of Science, University of Hradec Králové, Rokitanského 62, Hradec Králové, 530 03, Czech Republic; Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 532 10, Czech Republic
utb.fulltext.projects	IGA/FT/2020/007
utb.fulltext.faculty	Faculty of Technology
utb.fulltext.ou	Department of Chemistry