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    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.

    164077_164077.pdf (177.9Kb)
    Access Status
    Open access
    Authors
    Dolzhenko, Anton
    Tan, B.
    Dolzhenko, A.
    Chiu, G.
    Chui, W.
    Date
    2008
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Dolzhenko, Anton and Tan, Bee and Dolzhenko, Anna and Chiu, Gigi and Chui, Wai. 2008. 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.. Journal of Fluorine Chemistry. 129 (5): pp. 429-434.
    Source Title
    Journal of Fluorine Chemistry
    DOI
    10.1016/j.jfluchem.2008.02.007
    ISSN
    0022-1139
    School
    School of Pharmacy
    Remarks

    NOTICE: This is the author's version of a work that was accepted for publication in Journal of Fluorine Chemistry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Fluorine Chemistry, 129, 5, 2008. DOI: 10.1016/j.jfluchem.2008.02.007

    URI
    http://hdl.handle.net/20.500.11937/18598
    Collection
    • Curtin Research Publications
    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.

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