Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines

Anna Dolzhenko, Bee Jen Tan, Gigi Ngar Chee Chiu, Wai-Keung Chui, Anton V Dolzhenko

    Research output: Contribution to journalArticleResearchpeer-review

    8 Citations (Scopus)

    Abstract

    New fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines were designed as potential anticancer agents and a practical method for their preparation was developed. The reaction of benzhydrazide with cyanoguanidine followed by intramolecular cyclocondensation resulted in the formation of triazolylguanidine, which upon condensation with trichloroacetonitrile afforded a key intermediate - 2-phenyl-7-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine. In mild conditions, this intermediate underwent nucleophilic displacement of the trichloromethyl group with a series of fluorinated benzylamines providing the target compounds. Antiproliferative activity of the prepared compounds against the lung and breast cancer cells was explored. Together with anticancer effect, some compounds demonstrated anti-angiogenic properties.
    Original languageEnglish
    Pages (from-to)68 - 72
    Number of pages5
    JournalJournal of Fluorine Chemistry
    Volume175
    Issue numberJuly 2015
    DOIs
    Publication statusPublished - 2015

    Cite this

    Dolzhenko, Anna ; Tan, Bee Jen ; Chiu, Gigi Ngar Chee ; Chui, Wai-Keung ; Dolzhenko, Anton V. / Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines. In: Journal of Fluorine Chemistry. 2015 ; Vol. 175, No. July 2015. pp. 68 - 72.
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    title = "Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines",
    abstract = "New fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines were designed as potential anticancer agents and a practical method for their preparation was developed. The reaction of benzhydrazide with cyanoguanidine followed by intramolecular cyclocondensation resulted in the formation of triazolylguanidine, which upon condensation with trichloroacetonitrile afforded a key intermediate - 2-phenyl-7-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine. In mild conditions, this intermediate underwent nucleophilic displacement of the trichloromethyl group with a series of fluorinated benzylamines providing the target compounds. Antiproliferative activity of the prepared compounds against the lung and breast cancer cells was explored. Together with anticancer effect, some compounds demonstrated anti-angiogenic properties.",
    author = "Anna Dolzhenko and Tan, {Bee Jen} and Chiu, {Gigi Ngar Chee} and Wai-Keung Chui and Dolzhenko, {Anton V}",
    year = "2015",
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    language = "English",
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    }

    Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines. / Dolzhenko, Anna; Tan, Bee Jen; Chiu, Gigi Ngar Chee; Chui, Wai-Keung; Dolzhenko, Anton V.

    In: Journal of Fluorine Chemistry, Vol. 175, No. July 2015, 2015, p. 68 - 72.

    Research output: Contribution to journalArticleResearchpeer-review

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    AU - Dolzhenko, Anna

    AU - Tan, Bee Jen

    AU - Chiu, Gigi Ngar Chee

    AU - Chui, Wai-Keung

    AU - Dolzhenko, Anton V

    PY - 2015

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    AB - New fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines were designed as potential anticancer agents and a practical method for their preparation was developed. The reaction of benzhydrazide with cyanoguanidine followed by intramolecular cyclocondensation resulted in the formation of triazolylguanidine, which upon condensation with trichloroacetonitrile afforded a key intermediate - 2-phenyl-7-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine. In mild conditions, this intermediate underwent nucleophilic displacement of the trichloromethyl group with a series of fluorinated benzylamines providing the target compounds. Antiproliferative activity of the prepared compounds against the lung and breast cancer cells was explored. Together with anticancer effect, some compounds demonstrated anti-angiogenic properties.

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