Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.ejmech.2013.06.051
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
Authors: Bera, H.
Tan, B.J. 
Sun, L.
Dolzhenko, A.V. 
Chui, W.-K. 
Chiu, G.N.C. 
Keywords: 1,2,4-Triazolo[1,5-a][1,3,5]triazine
Anti-angiogenesis
Breast cancer
Mixed-type inhibition
SAR
Thymidine phosphorylase inhibitors
Issue Date: 2013
Citation: Bera, H., Tan, B.J., Sun, L., Dolzhenko, A.V., Chui, W.-K., Chiu, G.N.C. (2013). 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. European Journal of Medicinal Chemistry 67 : 325-334. ScholarBank@NUS Repository. https://doi.org/10.1016/j.ejmech.2013.06.051
Abstract: 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.
Source Title: European Journal of Medicinal Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/105597
ISSN: 02235234
DOI: 10.1016/j.ejmech.2013.06.051
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