Regioselectivity and tautomerism of novel five-membered ring nitrogen heterocycles formed via cyclocondensation of acylthiosemicarbazides.
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.
Tomasciková
Jana
J
Institute of Chemistry, Faculty of Science, P. J. Safárik University, SK-041 67 Kosice, Slovak Republic.
Imrich
Ján
J
Danihel
Ivan
I
Böhm
Stanislav
S
Kristian
Pavol
P
Pisarcíková
Jana
J
Sabol
Marián
M
Klika
Karel D
KD
D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D003500:Cyclization / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen / Q000737:chemistry*; D012663:Semicarbazides / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D006834:Hydrazines; D017879:Isothiocyanates; D012663:Semicarbazides; D009584:Nitrogen