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Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

1
Institute of Chemistry, Faculty of Science, P. J. Šafárik University, SK-041 67 Košice, Slovak Republic
2
Department of Organic Chemistry, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic
3
Institute of Medical and Clinical Microbiology, Faculty of Medicine, P. J. Šafárik University, SK-040 66 Košice, Slovak Republic
4
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
*
Author to whom correspondence should be addressed.
Molecules 2008, 13(3), 501-518; https://doi.org/10.3390/molecules13030501
Received: 19 February 2008 / Revised: 27 February 2008 / Accepted: 27 February 2008 / Published: 1 March 2008
A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including fournew compounds, were prepared in order to study substituent effects on cyclizationreactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethylacetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation underalkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f wasalso prepared. Altogether, twenty new compounds characterized and identified by IR, UV,1H, 13C and 2D NMR and quantum chemical calculations are described. The tautomerismof the products and regioselectivity of the reactions were evaluated. Compounds 3f−h,3h·2HCl, 7b,d and 10 were screened for cytotoxic activity against the L1210 leukemia cellline and all compounds, except for 3f, exhibited promising inhibitions of cell growth. View Full-Text
Keywords: Acylthiosemicarbazides; imidazolidine-4; 5-diones; thiazolidin-4-ones; 1; 2; 4-triazoles; acridines; cytotoxic activity. Acylthiosemicarbazides; imidazolidine-4; 5-diones; thiazolidin-4-ones; 1; 2; 4-triazoles; acridines; cytotoxic activity.
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Tomaščiková, J.; Imrich, J.; Danihel, I.; Böhm, S.; Kristian, P.; Pisarčíková, J.; Sabol, M.; Klika, K.D. Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides. Molecules 2008, 13, 501-518.

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