A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities
Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demo...
| Main Authors: | , , , , , |
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| Format: | Journal Article |
| Published: |
2013
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| Online Access: | http://hdl.handle.net/20.500.11937/4279 |
| _version_ | 1848744471035904000 |
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| author | Bera, H. Tan, B. Sun, L. Dolzhenko, Anton Chui, W. Chiu, G. |
| author_facet | Bera, H. Tan, B. Sun, L. Dolzhenko, Anton Chui, W. Chiu, G. |
| author_sort | Bera, H. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the 5-thioxo analogues of 1,2,4-triazolo[1,5-a][1,3,5]triazine exhibited a varying degree of inhibitory activity towards thymidine phosphorylase, comparable or better than reference compound, 7-Deazaxanthine (7-DX, 2) (IC 50 value = 42.63 µM). Moreover, compounds 5q and 6i displayed a mixed-type of inhibitory mechanism in the presence of variable concentrations of thymidine (dThd). In addition, selected compounds were found to have a noticeable inhibitory effect on the expression of angiogenesis markers, including VEGF and MMP-9 in MDA-MB-231 breast cancer cells. © 2013 Elsevier Masson SAS. All rights reserved. |
| first_indexed | 2025-11-14T06:01:59Z |
| format | Journal Article |
| id | curtin-20.500.11937-4279 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T06:01:59Z |
| publishDate | 2013 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-42792017-09-13T12:23:16Z A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities Bera, H. Tan, B. Sun, L. Dolzhenko, Anton Chui, W. Chiu, G. Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the 5-thioxo analogues of 1,2,4-triazolo[1,5-a][1,3,5]triazine exhibited a varying degree of inhibitory activity towards thymidine phosphorylase, comparable or better than reference compound, 7-Deazaxanthine (7-DX, 2) (IC 50 value = 42.63 µM). Moreover, compounds 5q and 6i displayed a mixed-type of inhibitory mechanism in the presence of variable concentrations of thymidine (dThd). In addition, selected compounds were found to have a noticeable inhibitory effect on the expression of angiogenesis markers, including VEGF and MMP-9 in MDA-MB-231 breast cancer cells. © 2013 Elsevier Masson SAS. All rights reserved. 2013 Journal Article http://hdl.handle.net/20.500.11937/4279 10.1016/j.ejmech.2013.06.051 restricted |
| spellingShingle | Bera, H. Tan, B. Sun, L. Dolzhenko, Anton Chui, W. Chiu, G. A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| title | A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| title_full | A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| title_fullStr | A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| title_full_unstemmed | A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| title_short | A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| title_sort | structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities |
| url | http://hdl.handle.net/20.500.11937/4279 |