Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines
Novel fluorinated 4-benzylamino-7-phenylpyrazolo[1,5-a]- [1,3,5]triazin-2-amines were prepared using an efficient and practical approach. The chemoselectivity of condensation of pyrazolylguanidine and trichloroacetonitrile was found to be solvent-dependent and, when conducted in toluene, this reacti...
| Main Authors: | , , , , |
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| Format: | Journal Article |
| Published: |
The Japan Institute of Heterocyclic Chemistry
2016
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| Online Access: | http://hdl.handle.net/20.500.11937/44647 |
| _version_ | 1848757061303664640 |
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| author | Lim, F. Kow, K. Yeo, E. Chow, S. Dolzhenko, Anton |
| author_facet | Lim, F. Kow, K. Yeo, E. Chow, S. Dolzhenko, Anton |
| author_sort | Lim, F. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | Novel fluorinated 4-benzylamino-7-phenylpyrazolo[1,5-a]- [1,3,5]triazin-2-amines were prepared using an efficient and practical approach. The chemoselectivity of condensation of pyrazolylguanidine and trichloroacetonitrile was found to be solvent-dependent and, when conducted in toluene, this reaction afforded 7-phenyl-4-trichloromethylpyrazolo[1,5-a]- [1,3,5]triazin-2-amine as the main product. This key intermediate underwent nucleophilic replacement of the trichloromethyl group with fluorinated benzylamines providing a series of the target compounds. Antiproliferative activity of the prepared compounds against Jurkat T cells was explored using MTS assay. Morphological changes observed in cells treated by the most potent compounds of this series, suggested that these compounds induced apoptosis in cells. |
| first_indexed | 2025-11-14T09:22:06Z |
| format | Journal Article |
| id | curtin-20.500.11937-44647 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T09:22:06Z |
| publishDate | 2016 |
| publisher | The Japan Institute of Heterocyclic Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-446472017-09-13T14:10:55Z Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines Lim, F. Kow, K. Yeo, E. Chow, S. Dolzhenko, Anton Novel fluorinated 4-benzylamino-7-phenylpyrazolo[1,5-a]- [1,3,5]triazin-2-amines were prepared using an efficient and practical approach. The chemoselectivity of condensation of pyrazolylguanidine and trichloroacetonitrile was found to be solvent-dependent and, when conducted in toluene, this reaction afforded 7-phenyl-4-trichloromethylpyrazolo[1,5-a]- [1,3,5]triazin-2-amine as the main product. This key intermediate underwent nucleophilic replacement of the trichloromethyl group with fluorinated benzylamines providing a series of the target compounds. Antiproliferative activity of the prepared compounds against Jurkat T cells was explored using MTS assay. Morphological changes observed in cells treated by the most potent compounds of this series, suggested that these compounds induced apoptosis in cells. 2016 Journal Article http://hdl.handle.net/20.500.11937/44647 10.3987/COM-16-13464 The Japan Institute of Heterocyclic Chemistry restricted |
| spellingShingle | Lim, F. Kow, K. Yeo, E. Chow, S. Dolzhenko, Anton Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines |
| title | Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines |
| title_full | Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines |
| title_fullStr | Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines |
| title_full_unstemmed | Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines |
| title_short | Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines |
| title_sort | synthesis and antileukemic activity of new fluorinated 5-aza-9-deazapurines |
| url | http://hdl.handle.net/20.500.11937/44647 |