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Literature summary extracted from

  • Bajaj, S.; Roy, P.P.; Singh, J.
    Synthesis, thymidine phosphorylase inhibitory and computational study of novel 1,3,4-oxadiazole-2-thione derivatives as potential anticancer agents (2018), Comput. Biol. Chem., 76, 151-160 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.4.2.4 3-(((4-chlorophenyl)amino)(phenyl)methyl)-5-(2,6-dimethylphenyl)1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 3-(((4-chlorophenyl)amino)methyl)-5-(2-iodophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 3-((4-benzylpiperazin-1-yl)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 3-((5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl)methyl)thiazolidine-2,4-dione
-
Homo sapiens
2.4.2.4 3-((benzylamino)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(2-chlorophenyl)-3-(((4-chlorophenyl)amino)(phenyl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(2-chlorophenyl)-3-((thiazol-2-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-(((2-nitrophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-(((3,3-diphenylpropyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-(((4-fluorophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-(((4-hydroxyphenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((2-methyl-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((4-cyclohexylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((cyclohexylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((dicyclohexylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((naphthalen-1-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((phenylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 5-(4-chlorophenyl)-3-((thiazol-2-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
Homo sapiens
2.4.2.4 7-deazaxanthine
-
Homo sapiens
2.4.2.4 additional information synthesis, thymidine phosphorylase inhibitory and computational study of 1,3,4-oxadiazole-2-thione derivatives as potential anticancer agents. Determination of growth inhibition of MCF-7 cells, and analysis of toxicity and pharmacokinetics in the human body. Docking study using the ligand-bound TP structure (PDB ID 1UOU). Structure-function analysis. Electron withdrawing groups at R1 position of phenyl ring and less bulky amines group at R2 position have better anticancer activity. Amine groups at R2 position play an important role in binding to the active site residues of enzyme TP Homo sapiens
2.4.2.4 N-((5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-yl)methyl)3(trifluoromethyl) benzamide
-
Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.4.2.4 thymine + 2-deoxy-alpha-D-ribose 1-phosphate Homo sapiens
-
thymidine + phosphate
-
r

Organism

EC Number Organism UniProt Comment Textmining
2.4.2.4 Homo sapiens P19971
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.4.2.4 MCF-7 cell
-
Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.4.2.4 thymine + 2-deoxy-alpha-D-ribose 1-phosphate
-
Homo sapiens thymidine + phosphate
-
r

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.4.2.4 25
-
assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.4.2.4 7.4
-
assay at Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.4.2.4 0.0228
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((dicyclohexylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0237
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-(((4-hydroxyphenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0256
-
pH 7.4, 25°C Homo sapiens N-((5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-yl)methyl)3(trifluoromethyl) benzamide
2.4.2.4 0.0297
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((2-methyl-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0303
-
pH 7.4, 25°C Homo sapiens 3-((benzylamino)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0384
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-(((2-nitrophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.03868
-
pH 7.4, 25°C Homo sapiens 7-deazaxanthine
2.4.2.4 0.0446
-
pH 7.4, 25°C Homo sapiens 3-(((4-chlorophenyl)amino)methyl)-5-(2-iodophenyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0464
-
pH 7.4, 25°C Homo sapiens 5-(2-chlorophenyl)-3-((thiazol-2-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0506
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((cyclohexylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0547
-
pH 7.4, 25°C Homo sapiens 3-((5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl)methyl)thiazolidine-2,4-dione
2.4.2.4 0.0582
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0693
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-(((3,3-diphenylpropyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0832
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((4-cyclohexylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.0872
-
pH 7.4, 25°C Homo sapiens 5-(2-chlorophenyl)-3-(((4-chlorophenyl)amino)(phenyl)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.1171
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((naphthalen-1-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.1505
-
pH 7.4, 25°C Homo sapiens 5-(4-chlorophenyl)-3-((thiazol-2-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
2.4.2.4 0.1833
-
pH 7.4, 25°C Homo sapiens 3-((4-benzylpiperazin-1-yl)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione

General Information

EC Number General Information Comment Organism
2.4.2.4 additional information the important residues of enzyme TP responsible for activity are Ser117, Ser217, His116, Lys221, Arg202, Tyr199, Thr118, Arg146, Leu148, Thr151, Gly152, and Ile214, computational structure-function analysis Homo sapiens