Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines
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...
| Main Authors: | , , , , |
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| Format: | Journal Article |
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Elsevier
2015
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| Online Access: | http://hdl.handle.net/20.500.11937/18632 |
| _version_ | 1848749800077393920 |
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| author | Dolzhenko, Anton Tan, B. Chiu, G. Chui, W. Dolzhenko, A. |
| author_facet | Dolzhenko, Anton Tan, B. Chiu, G. Chui, W. Dolzhenko, A. |
| author_sort | Dolzhenko, Anton |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T07:26:41Z |
| format | Journal Article |
| id | curtin-20.500.11937-18632 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T07:26:41Z |
| publishDate | 2015 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-186322017-09-13T13:46:03Z Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines Dolzhenko, Anton Tan, B. Chiu, G. Chui, W. Dolzhenko, A. 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. 2015 Journal Article http://hdl.handle.net/20.500.11937/18632 10.1016/j.jfluchem.2015.03.010 Elsevier restricted |
| spellingShingle | Dolzhenko, Anton Tan, B. Chiu, G. Chui, W. Dolzhenko, A. Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| title | Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| title_full | Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| title_fullStr | Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| title_full_unstemmed | Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| title_short | Synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| title_sort | synthesis and biological activity of fluorinated 7-benzylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines |
| url | http://hdl.handle.net/20.500.11937/18632 |