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Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid.
Klásek, Antonín; Lycka, Antonín; Kremen, Filip; Ruzicka, Ales; Rouchal, Michal.
Affiliation
  • Klásek A; Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavreckova 5669, 760 01 Zlín, Czech Republic.
  • Lycka A; Department of Chemistry, Faculty of Science, University of Hradec Králové, Rokitanského 62, 530 03 Hradec Králové, Czech Republic.
  • Kremen F; Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavreckova 5669, 760 01 Zlín, Czech Republic.
  • Ruzicka A; Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic.
  • Rouchal M; Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavreckova 5669, 760 01 Zlín, Czech Republic.
Int J Mol Sci ; 23(10)2022 May 13.
Article in En | MEDLINE | ID: mdl-35628291
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 1H, 13C, and 15N 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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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Magnetic Resonance Spectroscopy Language: En Journal: Int J Mol Sci Year: 2022 Document type: Article Affiliation country:
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Magnetic Resonance Spectroscopy Language: En Journal: Int J Mol Sci Year: 2022 Document type: Article Affiliation country: