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

Molecules

Jana Tomaščiková¹  Ján Imrich¹  Ivan Danihel¹  Stanislav Böhm²  Pavol Kristian¹  Jana Pisarčíková¹  Marián Sabol³ 

[1] Institute of Chemistry, Faculty of Science, P. J. Šafárik University, SK-041 67 Košice, Slovak Republic;Department of Organic Chemistry, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic;Institute of Medical and Clinical Microbiology, Faculty of Medicine, P. J. Šafárik University, SK-040 66 Košice, Slovak Republic

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

DOI  :  10.3390/molecules13030501

来源: mdpi

【 摘 要 】

A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including four new compounds, were prepared in order to study substituent effects on cyclization reactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethyl acetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation under alkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f was also prepared. Altogether, twenty new compounds characterized and identified by IR, UV, ¹H, ¹³C and 2D NMR and quantum chemical calculations are described. The tautomerism of 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 cell line and all compounds, except for 3f, exhibited promising inhibitions of cell growth.

【 授权许可】

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