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Title: Synthesis, anti-thymidine phosphorylase activity and molecular docking of 5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ones
Authors: Bera, H.
Lee, M.H.
Sun, L.
Dolzhenko, A.V. 
Chui, W.K. 
Keywords: Angiogenesis
Annulation reaction
Heterobicyclic system
In vitro enzyme assay
Molecular docking
Thymidine phosphorylase inhibitors
Issue Date: 2013
Citation: Bera, H., Lee, M.H., Sun, L., Dolzhenko, A.V., Chui, W.K. (2013). Synthesis, anti-thymidine phosphorylase activity and molecular docking of 5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ones. Bioorganic Chemistry 50 : 34-40. ScholarBank@NUS Repository.
Abstract: In our lead finding program, a series of 5-thioxo-[1,2,4]triazolo[1,5-a][1, 3,5]triazin-7-ones and their 5-thio-alkyl derivatives were designed and synthesized which contained different substituents at ortho-position of 2-phenyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the synthesized compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase (TP), comparable to reference compound, 7-Deazaxanthine (7-DX, 2) (IC50 value = 42.63 lM). The study also inferred that the ortho-substituted group at the phenyl ring and 5-thio-alkyl moiety imparted steric hindrance effects in the binding site of the enzyme, leading to a reduced inhibitory response. In addition, compound 3a was identified as a mixed-type inhibitor of TP. Moreover, computational docking study was performed to illustrate the important structural information on the plausible ligand-enzyme binding interactions. © 2013 Elsevier Inc. All rights reserved.
Source Title: Bioorganic Chemistry
ISSN: 00452068
DOI: 10.1016/j.bioorg.2013.07.004
Appears in Collections:Staff Publications

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