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Literature summary for 2.4.2.4 extracted from
- In silico binding analysis and SAR elucidations of newly designed benzopyrazine analogs as potent inhibitors of thymidine phosphorylase (2016), Bioorg. Chem., 68, 80-89 .
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (E)-2-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,4-diol | - |
Escherichia coli |  |
| (E)-2-(2-(2-chlorobenzylidene)hydrazinyl)quinoxaline | - |
Escherichia coli | |
| (E)-2-(2-(2-fluorobenzylidene)hydrazinyl)quinoxaline | - |
Escherichia coli | |
| (E)-2-(2-(3-chlorobenzylidene)hydrazinyl)quinoxaline | - |
Escherichia coli | |
| (E)-2-(2-(3-fluorobenzylidene)hydrazinyl)quinoxaline | - |
Escherichia coli | |
| (E)-2-(2-(4-fluorobenzylidene)hydrazinyl)quinoxaline | - |
Escherichia coli | |
| (E)-3-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,2-diol | - |
Escherichia coli | |
| (E)-3-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | - |
Escherichia coli | |
| (E)-4-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,2-diol | - |
Escherichia coli | |
| (E)-4-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,3-diol | - |
Escherichia coli | |
| (E)-4-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | - |
Escherichia coli | |
| (E)-4-methoxy-2-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | - |
Escherichia coli | |
| (E)-5-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,2,4-triol | - |
Escherichia coli | |
| (E)-5-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-2,4,6-triol | - |
Escherichia coli | |
| 7-deazaxanthine | docking conformation of the standard inhibitor in the active site of thymidine phosphorylase, modeling, overview. Modeling of the three-dimensional structures of piperazine derivatives | Escherichia coli | |
| additional information | design of benzopyrazine analogues as potent inhibitors of thymidine phosphorylase, synthesis of quinoxaline derivatives, overview. No inhibition by (E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(4-nitrobenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(2-methylbenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(3-methylbenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(4-methylbenzylidene)hydrazinyl)quinoxaline, (E)-5-methoxy-2-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol, (E)-2-methoxy-5-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol, (E)-2-(2-(3-methoxybenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(4-methoxybenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(pyridin-3-ylmethylene)hydrazinyl)quinoxaline, (E)-2-(2-(pyridin-4-ylmethylene)hydrazinyl)quinoxaline, (E)-2-(2-((1H-indol-3-yl)methylene)hydrazinyl)quinoxaline, and (E)-2-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | Escherichia coli |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| thymine + 2-deoxy-alpha-D-ribose 1-phosphate | Escherichia coli | - |
thymidine + phosphate | - |
r | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Escherichia coli | - |
- |
- |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| commercial preparation | - |
Escherichia coli | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| thymine + 2-deoxy-alpha-D-ribose 1-phosphate | - |
Escherichia coli | thymidine + phosphate | - |
r | |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 25 | - |
assay at | Escherichia coli |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.4 | - |
assay at | Escherichia coli |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.0032 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,4-diol | |
| 0.0086 | - |
pH 7.4, 25°C | Escherichia coli | (E)-4-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,3-diol | |
| 0.0091 | - |
pH 7.4, 25°C | Escherichia coli | (E)-4-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,2-diol | |
| 0.0334 | - |
pH 7.4, 25°C | Escherichia coli | (E)-4-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | |
| 0.0336 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-(2-(2-fluorobenzylidene)hydrazinyl)quinoxaline | |
| 0.0344 | - |
pH 7.4, 25°C | Escherichia coli | (E)-5-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,2,4-triol | |
| 0.0355 | - |
pH 7.4, 25°C | Escherichia coli | (E)-3-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-1,2-diol | |
| 0.0363 | - |
pH 7.4, 25°C | Escherichia coli | (E)-4-methoxy-2-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | |
| 0.0376 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-(2-(2-chlorobenzylidene)hydrazinyl)quinoxaline | |
| 0.0469 | - |
pH 7.4, 25°C | Escherichia coli | (E)-5-((2-(quinoxalin-2-yl)hydrazono)methyl)benzene-2,4,6-triol | |
| 0.0581 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-(2-(4-fluorobenzylidene)hydrazinyl)quinoxaline | |
| 0.0632 | - |
pH 7.4, 25°C | Escherichia coli | (E)-3-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol | |
| 0.0661 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-(2-(3-fluorobenzylidene)hydrazinyl)quinoxaline | |
| 0.0734 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-(2-(3-chlorobenzylidene)hydrazinyl)quinoxaline | |
| 0.0935 | - |
pH 7.4, 25°C | Escherichia coli | (E)-2-(2-(3-chlorobenzylidene)hydrazinyl)quinoxaline | |
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