Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.jfluchem.2008.02.007
Title: Synthesis and biological activity of fluorinated 7-aryl-2-pyridyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amines [1]
Authors: Dolzhenko, A.V. 
Tan, B.J. 
Dolzhenko, A.V. 
Chiu, G.N.C. 
Chui, W.K. 
Keywords: 1,2,4-Triazoles
1,3,5-Triazines
5-Azapurines
Anticancer activity
Guanidines
Hydrazides
Tautomerism
Issue Date: May-2008
Source: Dolzhenko, A.V., Tan, B.J., Dolzhenko, A.V., Chiu, G.N.C., Chui, W.K. (2008-05). Synthesis and biological activity of fluorinated 7-aryl-2-pyridyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amines [1]. Journal of Fluorine Chemistry 129 (5) : 429-434. ScholarBank@NUS Repository. https://doi.org/10.1016/j.jfluchem.2008.02.007
Abstract: In our lead finding program, 12 new fluorinated 7-aryl-2-pyridyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amines were prepared via a practical three-step procedure starting from (iso)nicotinic hydrazides. The fluorine substituted aryl fragment was introduced in the last step through cyclocondensation of N-(3-pyridyl-1,2,4-triazol-5-yl)guanidines and fluoro/trifluoromethyl substituted benzaldehydes. The structures of the compounds were confirmed by 1H and 13C NMR spectral data. The tautomeric preferences for the compounds were established using 2D NOESY experiments. The antiproliferative activity of the synthesized 1,2,4-triazolo[1,5-a][1,3,5]triazines was evaluated against breast, colon and lung cancer cell lines. The highest antiproliferative activity in the series was found for 2-(pyridine-3-yl)-7-(4-trifluoromethylphenyl)-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amine. The lack of inhibitory activity against bovine dihydrofolate reductase (DHFR) indicated that the antiproliferative activity was realized via other mechanisms. © 2008 Elsevier B.V. All rights reserved.
Source Title: Journal of Fluorine Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/106390
ISSN: 00221139
DOI: 10.1016/j.jfluchem.2008.02.007
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