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Literature summary for 3.4.22.51 extracted from

  • Espindola, J.W.; Cardoso, M.V.; Filho, G.B.; Oliveira E Silva, D.A.; Moreira, D.R.; Bastos, T.M.; Simone, C.A.; Soares, M.B.; Villela, F.S.; Ferreira, R.S.; Castro, M.C.; Pereira, V.R.; Murta, S.M.; Sales Junior, P.A.; Romanha, A.J.; Leite, A.C.
    Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain (2015), Eur. J. Med. Chem., 101, 818-835 .
    View publication on PubMed
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Inhibitors

Inhibitors Comment Organism Structure
(2E)-2-[1-([1,1'-biphenyl]-4-yl)-2-(4-bromophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 11.8% inhibition, 23°C, pH 5.5; 0.05 mM, 88.9% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-bromophenyl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 67.5% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-chlorophenyl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 53.1% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-fluorophenyl)ethylidene]-N-methylhydrazine-1-carbothioamide 0.05 mM, 30.0% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-fluorophenyl)ethylidene]-N-phenylhydrazine-1-carbothioamide 0.05 mM, 35.0% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-fluorophenyl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 38.7% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-methoxyphenyl)ethylidene]-N-methylhydrazine-1-carbothioamide 0.05 mM, 29.8% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-methoxyphenyl)ethylidene]-N-phenylhydrazine-1-carbothioamide 0.05 mM, 42.8% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-methoxyphenyl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 70.9% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(4-methylphenyl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 67.6% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2E)-2-[2-(4-bromophenoxy)-1-(naphthalen-1-yl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 73.6% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-(2-[([1,1'-biphenyl]-3-yl)oxy]-1-(4-bromophenyl)ethylidene)hydrazine-1-carbothioamide 0.05 mM, 65.4% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-(2-[([1,1'-biphenyl]-4-yl)oxy]-1-(4-bromophenyl)ethylidene)hydrazine-1-carbothioamide 0.05 mM, 63.7% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(2,3-dichlorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 81.8% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(2-chlorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 58.9% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(3,4-dichlorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 99.1% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(3-chloro-4-fluorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 93.7% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(3-chlorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM,51.8 % inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(3-methoxyphenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 62.8% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(4-chlorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 76.3% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(4-ethylphenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 75.1% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(4-fluorophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 84.0% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(4-iodophenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 63.3% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(4-methoxyphenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 75.8% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-(4-tert-butylphenoxy)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 85.3% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-phenoxyethylidene]hydrazine-1-carbothioamide 0.05 mM, 61.8% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-[(naphthalen-1-yl)oxy]ethylidene]hydrazine-1-carbothioamide
-
 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-[(naphthalen-2-yl)oxy]ethylidene]hydrazine-1-carbothioamide 0.05 mM, 72.1% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[1-(4-bromophenyl)-2-[4-(propan-2-yl)phenoxy]ethylidene]hydrazine-1-carbothioamide 0.05 mM, 49.7% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
(2Z)-2-[2-(3-bromophenoxy)-1-(4-bromophenyl)ethylidene]hydrazine-1-carbothioamide 0.05 mM, 81.3% inhibition, 23°C, pH 5.5 Trypanosoma cruzi
additional information apolar substituents or halogen atom substitution at the aryl position improved cruzain inhibition and antiparasitic activity in comparison to unsubstituted thiosemicarbazone Trypanosoma cruzi
N-(4-([(2Z)-2-(4-bromophenyl)-2-(2-carbamothioylhydrazinylidene)ethyl]oxy)phenyl)acetamide 0.05 mM, 80.7% inhibition, 23°C, pH 5.5 Trypanosoma cruzi

Organism

Organism UniProt Comment Textmining
Trypanosoma cruzi P25779
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
benzyloxycarbonyl-Phe-Arg-7-amido-4-methylcoumarin + H2O
-
 Trypanosoma cruzi benzyloxycarbonyl-Phe-Arg + 7-amino-4-methylcoumarin
-
 ?

Synonyms

Synonyms Comment Organism
cruzain
-
 Trypanosoma cruzi

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000008
-
 23°C, pH 5.5 Trypanosoma cruzi (2Z)-2-[1-(4-bromophenyl)-2-(3,4-dichlorophenoxy)ethylidene]hydrazine-1-carbothioamide
0.00007
-
 23°C, pH 5.5 Trypanosoma cruzi (2Z)-2-[1-(4-bromophenyl)-2-(3-chloro-4-fluorophenoxy)ethylidene]hydrazine-1-carbothioamide
0.0004
-
 23°C, pH 5.5 Trypanosoma cruzi (2Z)-2-[1-(4-bromophenyl)-2-(4-fluorophenoxy)ethylidene]hydrazine-1-carbothioamide
0.0006
-
 23°C, pH 5.5 Trypanosoma cruzi (2E)-2-[1-([1,1'-biphenyl]-4-yl)-2-(4-bromophenoxy)ethylidene]hydrazine-1-carbothioamide