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Synthesis, thymidine phosphorylase inhibition and molecular modeling studies of 1,3,4-oxadiazole-2-thione derivatives.

Bioorganic chemistry (2015-04-29)
Sohail Anjum Shahzad, Muhammad Yar, Marek Bajda, Lubna Shahzadi, Zulfiqar Ali Khan, Syed Ali Raza Naqvi, Sadaf Mutahir, Nasir Mahmood, Khalid Mohammed Khan
ABSTRACT

Thymidine phosphorylase (TP) inhibitors have attracted great attention due to their ability to suppress the tumors formation. In our ongoing research, a series of 1,3,4-oxadiazole-2-thione (1-12) has been synthesized under simple reaction conditions in good to excellent yields (86-98%) and their TP inhibition potential has also been evaluated. The majority of synthesized compounds showed moderate thymidine phosphorylase inhibitory activity with IC50 values ranging from 38.24±1.28 to 258.43±0.43μM, and 7-deazaxanthine (7DX) was used as a reference compound (IC50 38.68±4.42). The TP activity was very much dependent on the C-5 substituents; among this series the compound 6 bearing 4-hydroxyphenyl group was found to be the most active with IC50 38.24±1.28μM. Molecular docking studies revealed their binding mode.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Potassium bromide, SAJ first grade, 99.0-101.0%
Sigma-Aldrich
Potassium bromide, BioXtra, ≥99.0%
Sigma-Aldrich
Potassium bromide, JIS special grade, 99.0-100.2%
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Potassium bromide, anhydrous, powder, 99.95% trace metals basis
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, anhydrous, 99.9 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Potassium bromide, anhydrous, powder, 99.999% trace metals basis
Sigma-Aldrich
Potassium bromide, BioUltra, ≥99.5% (AT)
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.5 atom % D
Sigma-Aldrich
Thymidine Phosphorylase, recombinant from Escherichia coli, recombinant, expressed in E. coli, buffered aqueous solution, ≥900 units/mL, 0.2 μm filtered