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Literature summary for 3.4.24.69 extracted from

  • Li, B.; Pai, R.; Cardinale, S.C.; Butler, M.M.; Peet, N.P.; Moir, D.T.; Bavari, S.; Bowlin, T.L.
    Synthesis and biological evaluation of botulinum neurotoxin A protease inhibitors (2010), J. Med. Chem., 53, 2264-2276.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.4.24.69

Inhibitors

Inhibitors Comment Organism Structure
2-(4-(2,4-dichlorophenoxy)phenyl)-6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole
-
 Clostridium botulinum
2-(4-(2-chloro-4-cyanophenoxy)phenyl)-1H-indole-6-carbonitrile
-
 Clostridium botulinum
2-(4-(2-chloro-4-cyanophenoxy)phenyl)-6-(4,5-dihydro-1H-imidazol-2-yl)indole
-
 Clostridium botulinum
2-(4-(4-(6-(1,4,5,6-tetrahydropyrimidin-2-yl)benzo[b]thiophen-2-yl)phenoxy)phenyl)-1,4,5,6-tetrahydropyrimidine
-
 Clostridium botulinum
2-(4-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)phenoxy)phenyl)-4,5-dihydro-1H-imidazole
-
 Clostridium botulinum
2-(4-(4-(6-(5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)phenoxy)phenyl)-1,4,5,6-tetrahydropyrimidin-5-ol
-
 Clostridium botulinum
2-(4-(4-carbamoylphenoxy)phenyl)-1H-indole-6-carboxamide
-
 Clostridium botulinum
2-(4-(4-cyanophenoxy)phenyl)-1H-indole-6-carboximidamide
-
 Clostridium botulinum
2-(4-(4-cyanophenoxy)phenyl)indole-6-carbonitrile
-
 Clostridium botulinum
2-(4-(6-(1,4,5,6-tetrahydropyrimidin-2-yl)benzo[b]thiophen-2-yl)phenyl)-1,4,5,6-tetrahydropyrimidine
-
 Clostridium botulinum
2-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-phenyl)-4,5-dihydro-1H-imidazole
-
 Clostridium botulinum
2-(4-fluorophenyl)-1H-indole-6-carbonitrile
-
 Clostridium botulinum
2-(4-fluorophenyl)-1H-indole-6-carboxamide
-
 Clostridium botulinum
2-(4-fluorophenyl)-1H-indole-6-carboximidamide
-
 Clostridium botulinum
2-(4-methoxyphenyl)-1H-indole-6-carboxamide
-
 Clostridium botulinum
2-(4-methoxyphenyl)-1H-indole-6-carboximidamide
-
 Clostridium botulinum
2-(4-methoxyphenyl)-6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole
-
 Clostridium botulinum
2-(5-(4-cyanophenoxy)pyridin-2-yl)-1H-indole-6-carbonitrile
-
 Clostridium botulinum
2-(5-fluoro-2-pyridyl)-6-benzo[b]thiophenecarboxamide
-
 Clostridium botulinum
6-(1,4,5,6-tetrahydropyrimidin-2-yl)-2-(4-(4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenoxy)phenyl)-1H-benzo[d]imidazole
-
 Clostridium botulinum
6-(1,4,5,6-tetrahydropyrimidin-2-yl)-2-(4-(4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenoxy)phenyl)-1H-indole
-
 Clostridium botulinum
6-(1,4,5,6-tetrahydropyrimidin-2-yl)-2-{5-[4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenoxy]pyridin-2-yl}-1H-indole
-
 Clostridium botulinum
6-(3,4,5,6-tetrahydropyrimidin-2-yl)-2-(4-(3,4,5,6-tetrahydropyrimidin-2-yl)phenyl)-1H-indole
-
 Clostridium botulinum
6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-1H-indole
-
 Clostridium botulinum
6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-(4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy)phenyl)-1H-benzo[d]imidazole
-
 Clostridium botulinum
6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-(4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy)phenyl)-1H-indole
-
 Clostridium botulinum
6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-fluorophenyl)-1H-indole
-
 Clostridium botulinum
6-(4,5-dihydroimidazol-2-yl)-2-(5-(4-(4,5-dihydroimidazol-2-yl)phenoxy)pyridine-2-yl)indole
-
 Clostridium botulinum
6-chloro-2-(4-(4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy)-phenyl)-1H-indole
-
 Clostridium botulinum
cinnamic acid hydroxamate
-
 Clostridium botulinum
additional information development of specific potent inhibitors of BoNT/A light chain, structure-activity relationship studies, overview Clostridium botulinum
N'-(2-(dimethylamino)ethyl)-2-(4-(4-(N'-2-(dimethylaminoethyl)carbamimidoyl)phenoxy)phenyl)-1H-indole-6-carboximidamide
-
 Clostridium botulinum
N,N-bis(7-aminoheptyl)-1-benzyl-4-[3-(hydroxyamino)-3-oxopropyl]-5-(3-hydroxy-3,3-diphenylpropyl)-1H-pyrrole-2-carboxamide a tetrasubstituted pyrrole inhibitor Clostridium botulinum
N1-(6-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-pyridine-3-yl)ethane-1,2-diamine
-
 Clostridium botulinum
NSC 240898 NSC 240898, a potent BoNT/A LC endopeptidase inhibitor, 75% inhibition at 0.02 mM, no cytotoxicity Clostridium botulinum

Organism

Organism UniProt Comment Textmining
Clostridium botulinum
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
SNRTRIDEANK(Dnp)RA(S-(N-[4-methyl-7-dimethylamino-coumarin-3-yl]-carboxamidomethyl)-L-cysteine)RML + H2O a SNAP-25 peptide, residues 187-203, substrate BoNT/A LC FRET-based assay Clostridium botulinum SNRTRIDEANK(Dnp) + RA(S-(N-[4-methyl-7-dimethylamino-coumarin-3-yl]-carboxamidomethyl)-L-cysteine)RML
-
 ?

Synonyms

Synonyms Comment Organism
BoNT/A
-
 Clostridium botulinum
botulinum neurotoxin a
-
 Clostridium botulinum

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Clostridium botulinum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Clostridium botulinum

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0025
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum N'-(2-(dimethylamino)ethyl)-2-(4-(4-(N'-2-(dimethylaminoethyl)carbamimidoyl)phenoxy)phenyl)-1H-indole-6-carboximidamide
0.0071
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)phenoxy)phenyl)-4,5-dihydro-1H-imidazole
0.0073
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(4-(6-(5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)phenoxy)phenyl)-1,4,5,6-tetrahydropyrimidin-5-ol
0.011
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum NSC 240898
0.0125
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-(4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy)phenyl)-1H-indole
0.02
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-1H-indole
0.021
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(1,4,5,6-tetrahydropyrimidin-2-yl)-2-(4-(4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenoxy)phenyl)-1H-indole
0.0245
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-(4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy)phenyl)-1H-benzo[d]imidazole
0.025
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(4-cyanophenoxy)phenyl)-1H-indole-6-carboximidamide
0.025
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(2,4-dichlorophenoxy)phenyl)-6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole
0.028
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(1,4,5,6-tetrahydropyrimidin-2-yl)-2-(4-(4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenoxy)phenyl)-1H-benzo[d]imidazole
0.03
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(2-chloro-4-cyanophenoxy)phenyl)-6-(4,5-dihydro-1H-imidazol-2-yl)indole
0.043
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-phenyl)-4,5-dihydro-1H-imidazole
0.045
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-methoxyphenyl)-6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole
0.054
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(4-(6-(1,4,5,6-tetrahydropyrimidin-2-yl)benzo[b]thiophen-2-yl)phenoxy)phenyl)-1,4,5,6-tetrahydropyrimidine
0.056
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum N1-(6-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-pyridine-3-yl)ethane-1,2-diamine
0.067
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(1,4,5,6-tetrahydropyrimidin-2-yl)-2-{5-[4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenoxy]pyridin-2-yl}-1H-indole
0.069
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(4,5-dihydroimidazol-2-yl)-2-(5-(4-(4,5-dihydroimidazol-2-yl)phenoxy)pyridine-2-yl)indole
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(4-cyanophenoxy)phenyl)indole-6-carbonitrile
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(4-carbamoylphenoxy)phenyl)-1H-indole-6-carboxamide
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(5-(4-cyanophenoxy)pyridin-2-yl)-1H-indole-6-carbonitrile
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(2-chloro-4-cyanophenoxy)phenyl)-1H-indole-6-carbonitrile
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-chloro-2-(4-(4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy)-phenyl)-1H-indole
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-fluorophenyl)-1H-indole-6-carbonitrile
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-fluorophenyl)-1H-indole-6-carboxamide
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-fluorophenyl)-1H-indole-6-carboximidamide
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-fluorophenyl)-1H-indole
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-methoxyphenyl)-1H-indole-6-carboxamide
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-methoxyphenyl)-1H-indole-6-carboximidamide
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 6-(3,4,5,6-tetrahydropyrimidin-2-yl)-2-(4-(3,4,5,6-tetrahydropyrimidin-2-yl)phenyl)-1H-indole
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(4-(6-(1,4,5,6-tetrahydropyrimidin-2-yl)benzo[b]thiophen-2-yl)phenyl)-1,4,5,6-tetrahydropyrimidine
0.1
-
 pH 7.4, 37°C, BoNT/A light chain Clostridium botulinum 2-(5-fluoro-2-pyridyl)-6-benzo[b]thiophenecarboxamide