Application | Comment | Organism |
---|---|---|
pharmacology | trypanothione reductase plays a central role in the trypanosomatid parasites defense against oxidative stress, trypanothione reductase is a promising target for antitrypanosomal drugs, 2-iminobenzimidazole class are potent trypanothione reductase inhibitors against Trypanosoma brucei rhodesiense and low cytotoxicity against human cells | Trypanosoma brucei rhodesiense |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis(3-benzyl-1,3-dihydro-2H-benzimidazol-2-imine) | - |
Trypanosoma brucei rhodesiense | |
1,1'-[methanediylbis(oxyethane-2,1-diyl)]bis(3-methyl-1,3-dihydro-2H-benzimidazol-2-imine) | IC50: 0.1 mM | Trypanosoma brucei | |
1,1'-[methanediylbis(oxyethane-2,1-diyl)]bis(3-phenyl-1,3-dihydro-2H-benzimidazol-2-imine) | IC50: 0.004 mM | Trypanosoma brucei | |
1-(1-methylpiperidin-3-yl)-3-(2-phenoxyethyl)-1,3-dihydro-2H-benzimidazol-2-imine | IC50: 0.1 mM | Trypanosoma brucei | |
1-(2,4-dichlorophenoxy)-3-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]propan-2-ol | IC50: 0.005 mM | Trypanosoma brucei | |
1-(2-phenoxyethyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-imine | IC50: 0.004 mM | Trypanosoma brucei | |
1-(3,4-dichlorophenyl)-2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | IC50: 0.004 mM | Trypanosoma brucei | |
1-(3,4-dichlorophenyl)-2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | - |
Trypanosoma brucei rhodesiense | |
1-(3,4-dichlorophenyl)-2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | IC50: 0.009 mM | Trypanosoma brucei | |
1-(3,4-dichlorophenyl)-2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanone | IC50: 0.01 mM | Trypanosoma brucei | |
1-(3,4-dichlorophenyl)-2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | IC50: 0.01 mM, 92% inhibition at 0.025 mM | Trypanosoma brucei | |
1-(3,4-dichlorophenyl)-2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | - |
Trypanosoma brucei rhodesiense | |
1-(3-phenoxypropyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-imine | IC50: 0.007 mM | Trypanosoma brucei | |
1-(4-bromophenyl)-2-(3-butyl-2-imino-2,3-dihydro-1H-benzimidazol-1-yl)ethanol | IC50: 0.1 mM, 42% inhibition at 0.025 mM | Trypanosoma brucei | |
1-(4-ethoxyphenyl)-2-(2-imino-3-prop-2-en-1-yl-2,3-dihydro-1H-benzimidazol-1-yl)ethanol | IC50: 0.1 mM, 6% inhibition at 0.025 mM | Trypanosoma brucei | |
1-(5-phenoxypentyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-imine | IC50: 0.008 mM | Trypanosoma brucei | |
1-biphenyl-4-yl-2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanone | IC50: 0.025 mM | Trypanosoma brucei | |
1-[2-imino-3-(2-morpholin-4-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-phenoxypropan-2-ol | IC50: 0.1 mM | Trypanosoma brucei | |
1-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3,3-dimethylbutan-2-ol | IC50: 0.1 mM, 66% inhibition at 0.025 mM | Trypanosoma brucei | |
1-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-(4-methoxyphenoxy)propan-2-ol | IC50: 0.016 mM | Trypanosoma brucei | |
1-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-phenoxypropan-2-ol | IC50: 0.005 mM | Trypanosoma brucei | |
1-[2-imino-3-(morpholin-4-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-(4-methylphenoxy)propan-2-ol | IC50: 0.1 mM | Trypanosoma brucei | |
1-[2-imino-3-(piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-(4-methylphenoxy)propan-2-ol | IC50: 0.009 mM | Trypanosoma brucei | |
2,2'-(2-imino-1H-benzimidazole-1,3(2H)-diyl)bis(N,N-diethylethanamine) | IC50: 0.059 mM | Trypanosoma brucei | |
2-(3-benzyl-2-imino-2,3-dihydro-1H-benzimidazol-1-yl)-1-(4-chlorophenyl)ethanol | IC50: 0.1 mM, 32% inhibition at 0.025 mM | Trypanosoma brucei | |
2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methoxyphenyl)ethanol | IC50: 0.024 mM, 85% inhibition at 0.025 mM | Trypanosoma brucei | |
2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methoxyphenyl)ethanone | IC50: 0.007 mM, 91% inhibition at 0.025 mM | Trypanosoma brucei | |
2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methylphenyl)ethanol | IC50: 0.019 mM | Trypanosoma brucei | |
2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methylphenyl)ethanol | IC50: 0.029 mM | Trypanosoma brucei | |
2-[3-[2-(dimethylamino)propyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methylphenyl)ethanol | IC50: 0.035 mM | Trypanosoma brucei | |
N,N-diethyl-2-(2-imino-3-prop-2-en-1-yl-2,3-dihydro-1H-benzimidazol-1-yl)ethanamine | IC50: 0.1 mM, 31% inhibition at 0.025 mM | Trypanosoma brucei | |
N,N-diethyl-2-[2-imino-3-(2-phenoxyethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanamine | IC50: 0.008 mM | Trypanosoma brucei | |
N-(2-phenoxyethyl)-N'-(2-piperidin-1-ylethyl)benzene-1,2-diamine | IC50: 0.1 mM | Trypanosoma brucei | |
N-[(2E)-1-(2-phenoxyethyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-ylidene]acetamide | IC50: 0.1 mM | Trypanosoma brucei |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Trypanosoma brucei | - |
Trypanosoma brucei rhodesiense | - |
Trypanosoma brucei rhodesiense | - |
- |
- |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
trypanothione + NADP+ | high-throughput screening campaign of a library of 100000 lead-like compounds identified 2-iminobenzimidazoles as a novel class of trypanothione reductase inhibitors | Trypanosoma brucei rhodesiense | trypanothione disulfide + NADPH + H+ | - |
? | |
trypanothione disulfide + NADPH | - |
Trypanosoma brucei | trypanothione + NADP+ | - |
? |
Synonyms | Comment | Organism |
---|---|---|
TR | - |
Trypanosoma brucei |
trypanothione reductase | - |
Trypanosoma brucei |
trypanothione reductase | TR | Trypanosoma brucei rhodesiense |
trypanothione-disulfide reductase | - |
Trypanosoma brucei rhodesiense |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
NADPH | - |
Trypanosoma brucei |
Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|
0.0019 | - |
1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis(3-benzyl-1,3-dihydro-2H-benzimidazol-2-imine) | - |
Trypanosoma brucei rhodesiense | |
0.0036 | - |
1-(3,4-dichlorophenyl)-2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | - |
Trypanosoma brucei rhodesiense | |
0.0054 | - |
1-(3,4-dichlorophenyl)-2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | - |
Trypanosoma brucei rhodesiense |
IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|
0.0002 | - |
- |
Trypanosoma brucei rhodesiense | 1-(3,4-dichlorophenyl)-2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | |
0.0006 | - |
- |
Trypanosoma brucei rhodesiense | 1-(3,4-dichlorophenyl)-2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | |
0.0013 | - |
- |
Trypanosoma brucei rhodesiense | 1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis(3-benzyl-1,3-dihydro-2H-benzimidazol-2-imine) | |
0.004 | - |
IC50: 0.004 mM | Trypanosoma brucei | 1-(3,4-dichlorophenyl)-2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | |
0.004 | - |
IC50: 0.004 mM | Trypanosoma brucei | 1-(2-phenoxyethyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-imine | |
0.004 | - |
IC50: 0.004 mM | Trypanosoma brucei | 1,1'-[methanediylbis(oxyethane-2,1-diyl)]bis(3-phenyl-1,3-dihydro-2H-benzimidazol-2-imine) | |
0.005 | - |
IC50: 0.005 mM | Trypanosoma brucei | 1-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-phenoxypropan-2-ol | |
0.005 | - |
IC50: 0.005 mM | Trypanosoma brucei | 1-(2,4-dichlorophenoxy)-3-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]propan-2-ol | |
0.007 | - |
IC50: 0.007 mM | Trypanosoma brucei | 1-(3-phenoxypropyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-imine | |
0.007 | - |
IC50: 0.007 mM, 91% inhibition at 0.025 mM | Trypanosoma brucei | 2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methoxyphenyl)ethanone | |
0.008 | - |
IC50: 0.008 mM | Trypanosoma brucei | N,N-diethyl-2-[2-imino-3-(2-phenoxyethyl)-2,3-dihydro-1H-benzimidazol-1-yl]ethanamine | |
0.008 | - |
IC50: 0.008 mM | Trypanosoma brucei | 1-(5-phenoxypentyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-imine | |
0.009 | - |
IC50: 0.009 mM | Trypanosoma brucei | 1-[2-imino-3-(piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-(4-methylphenoxy)propan-2-ol | |
0.009 | - |
IC50: 0.009 mM | Trypanosoma brucei | 1-(3,4-dichlorophenyl)-2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | |
0.01 | - |
IC50: 0.01 mM | Trypanosoma brucei | 1-(3,4-dichlorophenyl)-2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanone | |
0.01 | - |
IC50: 0.01 mM, 92% inhibition at 0.025 mM | Trypanosoma brucei | 1-(3,4-dichlorophenyl)-2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanol | |
0.016 | - |
IC50: 0.016 mM | Trypanosoma brucei | 1-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-(4-methoxyphenoxy)propan-2-ol | |
0.019 | - |
IC50: 0.019 mM | Trypanosoma brucei | 2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methylphenyl)ethanol | |
0.024 | - |
IC50: 0.024 mM, 85% inhibition at 0.025 mM | Trypanosoma brucei | 2-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methoxyphenyl)ethanol | |
0.025 | - |
IC50: 0.025 mM | Trypanosoma brucei | 1-biphenyl-4-yl-2-[3-[2-(diethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]ethanone | |
0.029 | - |
IC50: 0.029 mM | Trypanosoma brucei | 2-[3-[2-(dimethylamino)ethyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methylphenyl)ethanol | |
0.035 | - |
IC50: 0.035 mM | Trypanosoma brucei | 2-[3-[2-(dimethylamino)propyl]-2-imino-2,3-dihydro-1H-benzimidazol-1-yl]-1-(4-methylphenyl)ethanol | |
0.059 | - |
IC50: 0.059 mM | Trypanosoma brucei | 2,2'-(2-imino-1H-benzimidazole-1,3(2H)-diyl)bis(N,N-diethylethanamine) | |
0.1 | - |
IC50: 0.1 mM | Trypanosoma brucei | 1-[2-imino-3-(2-morpholin-4-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-phenoxypropan-2-ol | |
0.1 | - |
IC50: 0.1 mM | Trypanosoma brucei | 1-[2-imino-3-(morpholin-4-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3-(4-methylphenoxy)propan-2-ol | |
0.1 | - |
IC50: 0.1 mM | Trypanosoma brucei | 1,1'-[methanediylbis(oxyethane-2,1-diyl)]bis(3-methyl-1,3-dihydro-2H-benzimidazol-2-imine) | |
0.1 | - |
IC50: 0.1 mM | Trypanosoma brucei | N-(2-phenoxyethyl)-N'-(2-piperidin-1-ylethyl)benzene-1,2-diamine | |
0.1 | - |
IC50: 0.1 mM | Trypanosoma brucei | N-[(2E)-1-(2-phenoxyethyl)-3-(2-piperidin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-ylidene]acetamide | |
0.1 | - |
IC50: 0.1 mM | Trypanosoma brucei | 1-(1-methylpiperidin-3-yl)-3-(2-phenoxyethyl)-1,3-dihydro-2H-benzimidazol-2-imine | |
0.1 | - |
IC50: 0.1 mM, 31% inhibition at 0.025 mM | Trypanosoma brucei | N,N-diethyl-2-(2-imino-3-prop-2-en-1-yl-2,3-dihydro-1H-benzimidazol-1-yl)ethanamine | |
0.1 | - |
IC50: 0.1 mM, 32% inhibition at 0.025 mM | Trypanosoma brucei | 2-(3-benzyl-2-imino-2,3-dihydro-1H-benzimidazol-1-yl)-1-(4-chlorophenyl)ethanol | |
0.1 | - |
IC50: 0.1 mM, 42% inhibition at 0.025 mM | Trypanosoma brucei | 1-(4-bromophenyl)-2-(3-butyl-2-imino-2,3-dihydro-1H-benzimidazol-1-yl)ethanol | |
0.1 | - |
IC50: 0.1 mM, 6% inhibition at 0.025 mM | Trypanosoma brucei | 1-(4-ethoxyphenyl)-2-(2-imino-3-prop-2-en-1-yl-2,3-dihydro-1H-benzimidazol-1-yl)ethanol | |
0.1 | - |
IC50: 0.1 mM, 66% inhibition at 0.025 mM | Trypanosoma brucei | 1-[2-imino-3-(2-piperidin-1-ylethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-3,3-dimethylbutan-2-ol |