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Literature summary extracted from

  • Ngo, V.T.H.; Hoang, V.H.; Tran, P.T.; Van Manh, N.; Ann, J.; Kim, E.; Cui, M.; Choi, S.; Lee, J.; Kim, H.; Ha, H.J.; Choi, K.; Kim, Y.H.; Lee, J.
    Structure-activity relationship investigation of Phe-Arg mimetic region of human glutaminyl cyclase inhibitors (2018), Bioorg. Med. Chem., 26, 3133-3144 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.2.5 additional information structure-activity relationship analysis of Phe-Arg mimetic region of human glutaminyl cyclase inhibitors. Developed of QC inhibitors that contain 3-aminoalkyloxy-4-methoxyphenyl and 4-aminoalkyloxyphenyl groups to replace the previously developed pharmacophore, overview. In vivo activity of the compounds is analyzed using HT-22 cells, an immortalized hippocampal neuronal cell line Homo sapiens
2.3.2.5 N-((E)-4-(3-(4-(2-aminoethyl)piperazin-1-yl)-3-oxoprop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-((E)-4-(3-oxo-3-(piperazin-1-yl)prop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-((E)-4-(3-oxo-3-(piperidin-4-ylamino)prop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3,4-dimethoxyphenyl)-N'-[3-(5-methyl-1H-imidazol-1-yl)propyl]thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(2-(2-aminopyridin-4-yl)ethoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(2-aminoethoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(3-(2-aminopyridin-4-yl)propoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(3-aminopropoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(4-(2-aminopyridin-4-yl)butoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(4-(dimethylamino)butoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(3-(4-aminobutoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-((1-(2-aminoethyl)piperidin-4-yl)carbamoyl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-(2-(((2-aminopyridin-4-yl)methyl)amino)-2-oxoethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-(2-((1-(2-aminoethyl)piperidin-4-yl)amino)-2-oxoethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-(2-(piperazin-1-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-(2-oxo-2-(piperazin-1-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-(2-oxo-2-(piperidin-4-ylamino)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-(4-(2-aminopyridin-4-yl)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(2-(1-methylpiperidin-4-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(2-(piperazin-1-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(2-(piperidin-4-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(3-(methylamino)propoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(3-(piperazin-1-yl)propoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(3-(piperidin-4-yl)propoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(4-(methylamino)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(4-(piperazin-1-yl)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(4-(piperidin-4-yl)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(4-methoxy-3-(4-(pyrimidin-2-ylamino)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens
2.3.2.5 N-(E)-(4-(3-(4-(2-aminoethyl)piperazin-1-yl)-3-oxoprop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
-
 Homo sapiens

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.3.2.5 Zn2+ required Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.2.5 L-glutaminyl-peptide Homo sapiens
-
 5-oxoprolyl-peptide + NH3
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.2.5 Homo sapiens Q16769 isozyme sQC
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.2.5 hippocampus
-
 Homo sapiens
-
2.3.2.5 neuron
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.2.5 L-glutaminyl-peptide
-
 Homo sapiens 5-oxoprolyl-peptide + NH3
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.2.5 glutaminyl cyclase
-
 Homo sapiens
2.3.2.5 hQC
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.3.2.5 0.0000064
-
 pH and temperature not specified in the publication Homo sapiens N-((E)-4-(3-(4-(2-aminoethyl)piperazin-1-yl)-3-oxoprop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000073
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(2-(piperidin-4-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000079
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(2-aminoethoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000079
-
 pH and temperature not specified in the publication Homo sapiens N-(4-(2-((1-(2-aminoethyl)piperidin-4-yl)amino)-2-oxoethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000079
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(4-(piperidin-4-yl)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000088
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(4-aminobutoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000088
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(3-(piperidin-4-yl)propoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.000009
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(3-aminopropoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000112
-
 pH and temperature not specified in the publication Homo sapiens N-(E)-(4-(3-(4-(2-aminoethyl)piperazin-1-yl)-3-oxoprop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000114
-
 pH and temperature not specified in the publication Homo sapiens N-(4-(2-oxo-2-(piperazin-1-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000129
-
 pH and temperature not specified in the publication Homo sapiens N-(4-(2-oxo-2-(piperidin-4-ylamino)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.000015
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(3-(2-aminopyridin-4-yl)propoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.000015
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(4-(piperazin-1-yl)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000152
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(4-(pyrimidin-2-ylamino)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000158
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(3-(piperazin-1-yl)propoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000159
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(4-(2-aminopyridin-4-yl)butoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000162
-
 pH and temperature not specified in the publication Homo sapiens N-(4-((1-(2-aminoethyl)piperidin-4-yl)carbamoyl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000184
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(2-(piperazin-1-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000187
-
 pH and temperature not specified in the publication Homo sapiens N-(4-(2-(piperazin-1-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000194
-
 pH and temperature not specified in the publication Homo sapiens N-((E)-4-(3-oxo-3-(piperazin-1-yl)prop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000206
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(2-(1-methylpiperidin-4-yl)ethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.000022
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(4-(methylamino)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000247
-
 pH and temperature not specified in the publication Homo sapiens N-(4-(4-(2-aminopyridin-4-yl)butoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.000026
-
 pH and temperature not specified in the publication Homo sapiens N-((E)-4-(3-oxo-3-(piperidin-4-ylamino)prop-1-en-1-yl)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000264
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(2-(2-aminopyridin-4-yl)ethoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000268
-
 pH and temperature not specified in the publication Homo sapiens N-(4-methoxy-3-(3-(methylamino)propoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000292
-
 pH and temperature not specified in the publication Homo sapiens N-(3,4-dimethoxyphenyl)-N'-[3-(5-methyl-1H-imidazol-1-yl)propyl]thiourea
2.3.2.5 0.0000468
-
 pH and temperature not specified in the publication Homo sapiens N-(3-(4-(dimethylamino)butoxy)-4-methoxyphenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
2.3.2.5 0.0000565
-
 pH and temperature not specified in the publication Homo sapiens N-(4-(2-(((2-aminopyridin-4-yl)methyl)amino)-2-oxoethoxy)phenyl)-N'-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea