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Literature summary for 2.5.1.58 extracted from

  • Bosc, D.; Mouray, E.; Cojean, S.; Franco, C.H.; Loiseau, P.M.; Freitas-Junior, L.H.; Moraes, C.B.; Grellier, P.; Dubois, J.
    Highly improved antiparasitic activity after introduction of an N-benzylimidazole moiety on protein farnesyltransferase inhibitors (2016), Eur. J. Med. Chem., 109, 173-186.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylic acid
-
Homo sapiens
3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylic acid
-
Trypanosoma brucei
3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylic acid
-
Homo sapiens
3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylic acid
-
Trypanosoma brucei
3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylic acid
-
Homo sapiens
3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylic acid
-
Trypanosoma brucei
3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylic acid
-
Homo sapiens
3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylic acid
-
Trypanosoma brucei
4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylic acid
-
Homo sapiens
4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylic acid
-
Trypanosoma brucei
4-[[4-([[4-(4-chlorophenyl)-3-ethynylthiophen-2-yl]amino]methyl)-1H-imidazol-1-yl]methyl]benzonitrile
-
Homo sapiens
4-[[4-([[4-(4-chlorophenyl)-3-ethynylthiophen-2-yl]amino]methyl)-1H-imidazol-1-yl]methyl]benzonitrile
-
Trypanosoma brucei
5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylic acid
-
Homo sapiens
5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylic acid
-
Trypanosoma brucei
5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
-
Homo sapiens
5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
-
Trypanosoma brucei
5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
-
Homo sapiens
5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
-
Trypanosoma brucei
5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
-
Homo sapiens
5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
-
Trypanosoma brucei
ethyl 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylate
-
Homo sapiens
ethyl 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylate
-
Trypanosoma brucei
ethyl 3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylate
-
Homo sapiens
ethyl 3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylate
-
Trypanosoma brucei
ethyl 3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylate
-
Homo sapiens
ethyl 3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylate
-
Trypanosoma brucei
ethyl 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl]amino)-4-ethynylthiophene-2-carboxylate
-
Homo sapiens
ethyl 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylate
-
Homo sapiens
ethyl 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylate
-
Trypanosoma brucei
ethyl 4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylate
-
Homo sapiens
ethyl 4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylate
-
Trypanosoma brucei
ethyl 5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylate
-
Homo sapiens
ethyl 5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylate
-
Trypanosoma brucei
ethyl 5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
-
Homo sapiens
ethyl 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
-
Homo sapiens
ethyl 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
-
Homo sapiens
ethyl 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
-
Trypanosoma brucei
methyl N-([5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophen-2-yl]carbonyl)-L-methioninate
-
Homo sapiens
methyl N-[[3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophen-2-yl]carbonyl]-L-methioninate
-
Homo sapiens
methyl N-[[3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophen-2-yl]carbonyl]-L-methioninate
-
Trypanosoma brucei
methyl N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methioninate
-
Homo sapiens
methyl N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methioninate
-
Trypanosoma brucei
additional information introduction of an N-benzylimidazole moiety on protein farnesyltransferase inhibitors highly improves their antiparasitic activity against parasite cell proliferation, e.g. of Plasmodium falciparum, Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, overview. Generally compounds of the arylthiophene series are not very active on Plasmodium falciparum. No inhibition by ethyl 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylate and methyl N-[[3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophen-2-yl]carbonyl]-L-methioninate Homo sapiens
additional information introduction of an N-benzylimidazole moiety on protein farnesyltransferase inhibitors highly improves their antiparasitic activity against parasite cell proliferation, e.g. of Plasmodium falciparum, Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, overview. Generally compounds of the arylthiophene series are not very active on Plasmodium falciparum. No inhibition by ethyl 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylate, methyl N-[[3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophen-2-yl]carbonyl]-L-methioninate, ethyl 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl]amino)-4-ethynylthiophene-2-carboxylate, ethyl 5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate, methyl N-([5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophen-2-yl]carbonyl)-L-methioninate, and ethyl 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate Trypanosoma brucei
N-[[3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophen-2-yl]carbonyl]-L-methionine
-
Homo sapiens
N-[[3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophen-2-yl]carbonyl]-L-methionine
-
Trypanosoma brucei
N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methionine
-
Homo sapiens
N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methionine
-
Trypanosoma brucei

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Homo sapiens
Mg2+ required Trypanosoma brucei
Zn2+ required Homo sapiens
Zn2+ required Trypanosoma brucei

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2E,6E)-farnesyl diphosphate + [protein]-L-cysteine Homo sapiens
-
S-(2E,6E)-farnesyl-[protein]-L-cysteine + diphosphate
-
?
(2E,6E)-farnesyl diphosphate + [protein]-L-cysteine Trypanosoma brucei
-
S-(2E,6E)-farnesyl-[protein]-L-cysteine + diphosphate
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Trypanosoma brucei
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2E,6E)-farnesyl diphosphate + [protein]-L-cysteine
-
Homo sapiens S-(2E,6E)-farnesyl-[protein]-L-cysteine + diphosphate
-
?
(2E,6E)-farnesyl diphosphate + [protein]-L-cysteine
-
Trypanosoma brucei S-(2E,6E)-farnesyl-[protein]-L-cysteine + diphosphate
-
?

Synonyms

Synonyms Comment Organism
hFTase
-
Homo sapiens
TbFTase
-
Trypanosoma brucei

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Homo sapiens
30
-
assay at Trypanosoma brucei

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Homo sapiens
7.5
-
assay at Trypanosoma brucei

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00001
-
pH 7.5, 30°C Homo sapiens 4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylic acid
0.000013
-
pH 7.5, 30°C Homo sapiens ethyl 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylate
0.000077
-
pH 7.5, 30°C Homo sapiens N-[[3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophen-2-yl]carbonyl]-L-methionine
0.00012
-
pH 7.5, 30°C Trypanosoma brucei N-[[3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophen-2-yl]carbonyl]-L-methionine
0.00013
-
pH 7.5, 30°C Homo sapiens ethyl 5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylate
0.00015
-
pH 7.5, 30°C Homo sapiens methyl N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methioninate
0.00019
-
pH 7.5, 30°C Homo sapiens ethyl 4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylate
0.00029
-
pH 7.5, 30°C Homo sapiens ethyl 5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
0.00033
-
pH 7.5, 30°C Homo sapiens ethyl 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
0.00037
-
pH 7.5, 30°C Homo sapiens 5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylic acid
0.00038
-
pH 7.5, 30°C Homo sapiens 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
0.00064
-
pH 7.5, 30°C Homo sapiens 5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
0.00068
-
pH 7.5, 30°C Homo sapiens methyl N-([5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophen-2-yl]carbonyl)-L-methioninate
0.00094
-
pH 7.5, 30°C Trypanosoma brucei 3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylic acid
0.00097
-
pH 7.5, 30°C Homo sapiens 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylic acid
0.00098
-
pH 7.5, 30°C Homo sapiens 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
0.001
-
pH 7.5, 30°C Trypanosoma brucei ethyl 3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylate
0.0012
-
pH 7.5, 30°C Homo sapiens ethyl 3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylate
0.0012
-
pH 7.5, 30°C Homo sapiens 3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophene-2-carboxylic acid
0.0017
-
pH 7.5, 30°C Trypanosoma brucei methyl N-[[3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophen-2-yl]carbonyl]-L-methioninate
0.0021
-
pH 7.5, 30°C Homo sapiens ethyl 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylate
0.0036
-
pH 7.5, 30°C Homo sapiens N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methionine
0.0046
-
pH 7.5, 30°C Homo sapiens methyl N-[[3-(4-chlorophenyl)-4-ethynyl-5-(2l5-triaz-1-en-2-yn-1-yl)thiophen-2-yl]carbonyl]-L-methioninate
0.0051
-
pH 7.5, 30°C Homo sapiens 4-[[4-([[4-(4-chlorophenyl)-3-ethynylthiophen-2-yl]amino]methyl)-1H-imidazol-1-yl]methyl]benzonitrile
0.0074
-
pH 7.5, 30°C Trypanosoma brucei ethyl 4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylate
0.01
-
pH 7.5, 30°C Trypanosoma brucei 4-ethynyl-5-([[1-(4-nitrobenzyl)-1H-imidazol-5-yl]methyl]amino)-3-phenylthiophene-2-carboxylic acid
0.011
-
pH 7.5, 30°C Trypanosoma brucei 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylic acid
0.013
-
pH 7.5, 30°C Trypanosoma brucei 3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylic acid
0.014
-
pH 7.5, 30°C Trypanosoma brucei ethyl 3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylate
0.015
-
pH 7.5, 30°C Trypanosoma brucei methyl N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methioninate
0.016
-
pH 7.5, 30°C Homo sapiens 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylic acid
0.018
-
pH 7.5, 30°C Trypanosoma brucei 5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophene-2-carboxylic acid
0.021
-
pH 7.5, 30°C Homo sapiens ethyl 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylate
0.022
-
pH 7.5, 30°C Homo sapiens 3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylic acid
0.031
-
pH 7.5, 30°C Trypanosoma brucei ethyl 3-(4-chlorophenyl)-4-cyano-5-(propan-2-ylsulfanyl)thiophene-2-carboxylate
0.034
-
pH 7.5, 30°C Homo sapiens ethyl 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl]amino)-4-ethynylthiophene-2-carboxylate
0.036
-
pH 7.5, 30°C Trypanosoma brucei 5-[(tert-butoxycarbonyl)[[1-(4-nitrobenzyl)-1H-imidazol-4-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
0.04
-
pH 7.5, 30°C Trypanosoma brucei N-[[5-([[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynyl-3-phenylthiophen-2-yl]carbonyl]-L-methionine
0.055
-
pH 7.5, 30°C Trypanosoma brucei 5-[(tert-butoxycarbonyl)[[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino]-3-(4-chlorophenyl)-4-ethynylthiophene-2-carboxylic acid
0.064
-
pH 7.5, 30°C Trypanosoma brucei 3-(4-chlorophenyl)-5-([[1-(4-cyanobenzyl)-1H-imidazol-4-yl]methyl][[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl]amino)-4-ethynylthiophene-2-carboxylic acid
0.1
-
pH 7.5, 30°C Homo sapiens ethyl 3-(4-chlorophenyl)-4-ethynyl-5-[(1H-imidazol-4-ylacetyl)amino]thiophene-2-carboxylate