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• Tomaščiková, J
• Imrich, J
• Danihel, I
• Böhm, S
• Kristian, P
• Pisarčíková, J
• Sabol, M
• Klika, KD.
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• Tomaščiková, J
• Imrich, J
• Danihel, I
• Böhm, S
• Kristian, P
• Pisarčíková, J
• Sabol, M
• Klika, KD.
• [+] on PubMed
• Tomaščiková, J
• Imrich, J
• Danihel, I
• Böhm, S
• Kristian, P
• Pisarčíková, J
• Sabol, M
• Klika, KD.

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Molecules 2008, 13(3), 501-518; doi:10.3390/molecules13030501

Article

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

Jana Tomaščiková ¹ , Ján Imrich ^1,* , Ivan Danihel ¹ , Stanislav Böhm ² , Pavol Kristian ¹ , Jana Pisarčíková ¹ , Marián Sabol ³  and Karel D. Klika ⁴

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.

Received: 19 February 2008; in revised form: 27 February 2008 / Accepted: 27 February 2008 / Published: 1 March 2008

Download PDF Full-Text [121 KB, uploaded 1 October 2008 09:18 CEST]

Abstract: 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.

Keywords: Acylthiosemicarbazides; imidazolidine-4; 5-diones; thiazolidin-4-ones; 1; 2; 4-triazoles; acridines; cytotoxic activity.

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