Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 4.2.2.1 extracted from

  • Braun, S.; Botzki, A.; Salmen, S.; Textor, C.; Bernhardt, G.; Dove, S.; Buschauer, A.
    Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase (2011), Eur. J. Med. Chem., 46, 4419-4429.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(3-chlorophenyl)(2-thioxo-1H-benzo[d]imidazol-1-yl)methanone
-
Streptococcus agalactiae
(E)-3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)prop-2-en-1-one 36% inhibition Streptococcus agalactiae
1,3-benzoxazole-2(3H)-thione
-
Streptococcus agalactiae
1,3-diacetyl-1H-benzo[d]imidazol-2(3H)-one 10% inhibition Streptococcus agalactiae
1,3-diacetylbenzimidazole-2-thione
-
Streptococcus agalactiae
1,3-dihydro-2H-benzimidazole-2-thione
-
Streptococcus agalactiae
1-(2-thioxo-1H-benzo[d]imidazol-1-yl)-3-phenylpropan-1-one
-
Streptococcus agalactiae
1-(2-thioxo-1H-benzo[d]imidazol-1-yl)butan-1-one
-
Streptococcus agalactiae
1-(2-thioxo-1H-benzo[d]imidazol-1-yl)ethanone
-
Streptococcus agalactiae
1-(2-thioxo-1H-benzo[d]imidazol-1-yl)hexan-1-one
-
Streptococcus agalactiae
1-(2-thioxo-1H-benzo[d]imidazol-1-yl)propan-1one
-
Streptococcus agalactiae
1-(2-thioxobenzo[d]oxazol-3(2H)-yl)decan-1-one
-
Streptococcus agalactiae
1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
-
Streptococcus agalactiae
1-(2-thioxobenzo[d]oxazol-3(2H)-yl)hexadecan-1-one
-
Streptococcus agalactiae
1-(2-thioxobenzo[d]oxazol-3(2H)-yl)hexan-1-one
-
Streptococcus agalactiae
1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
-
Streptococcus agalactiae
1-(3-acetyl-1,2-dihydro-2-thioxobenzo[d]imidazol-1-yl)hexan-1-one
-
Streptococcus agalactiae
1-(3-ethyl-1,2-dihydro-2-thioxobenzo[d]imidazole-1-yl)ethanone
-
Streptococcus agalactiae
1-ethyl-1H-benzo[d]imidazole-2(3H)-thione 28% inhibition Streptococcus agalactiae
2-phenoxy-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
-
Streptococcus agalactiae
2-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
-
Streptococcus agalactiae
3-acetylbenzo[d]oxazol-2(3H)-one
-
Streptococcus agalactiae
3-cyclohexyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
-
Streptococcus agalactiae
3-ethylbenzo[d]oxazole-2(3H)-thione 17% inhibition Streptococcus agalactiae
3-hexanoylbenzo[d]oxazol-2(3H)-one
-
Streptococcus agalactiae
3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
-
Streptococcus agalactiae
4-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)butan-1-one
-
Streptococcus agalactiae
benzyl 2-thioxobenzo[d]oxazol-3(2H)-carboxylate
-
Streptococcus agalactiae
methyl 2-sulfanylbenzo[d]oxazole-5-carboxylate 27% inhibition Streptococcus agalactiae
methyl-3-(3-phenylpropanoyl)-2,3-dihydro-2-thioxobenzo[d]oxazole-5-carboxylate
-
Streptococcus agalactiae
additional information development of structure-based 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones inhibitors, using the crystal structure of Streptococcus pneumoniae Hyal, overview. Except for N-(3-phenylpropionyl)benzoxazole-2-thione, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5.0. The compounds show a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch, overview. No inhibition by 3-hexanoylbenzo[d]oxazol-2(3H)-one. Inhibition at pH 5.0, structure-activity relationships, overview Streptococcus agalactiae
N-(3-phenylpropionyl)benzoxazole-2-thione
-
Streptococcus agalactiae

Organism

Organism UniProt Comment Textmining
Streptococcus agalactiae
-
-
-
Streptococcus agalactiae 4755
-
-
-

Synonyms

Synonyms Comment Organism
Hyal
-
Streptococcus agalactiae
hyaluronan lyase
-
Streptococcus agalactiae

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Streptococcus agalactiae

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
5 7.4 assay at Streptococcus agalactiae

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0001
-
pH 7.4, temperature not specified in the publication Streptococcus agalactiae 1,3-diacetyl-1H-benzo[d]imidazol-2(3H)-one
0.005
-
pH 7.4, temperature not specified in the publication Streptococcus agalactiae 1,3-diacetylbenzimidazole-2-thione
0.012
-
pH 7.4, temperature not specified in the publication Streptococcus agalactiae 1-(3-acetyl-1,2-dihydro-2-thioxobenzo[d]imidazol-1-yl)hexan-1-one
0.015
-
pH 5.0, 37°C Streptococcus agalactiae N-(3-phenylpropionyl)benzoxazole-2-thione
0.016
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxo-1H-benzo[d]imidazol-1-yl)hexan-1-one
0.017
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxo-1H-benzo[d]imidazol-1-yl)ethanone
0.017
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxobenzo[d]oxazol-3(2H)-yl)hexadecan-1-one
0.019
-
pH 7.4, 37°C Streptococcus agalactiae 4-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)butan-1-one
0.019
-
pH 7.4, temperature not specified in the publication Streptococcus agalactiae 1-(3-ethyl-1,2-dihydro-2-thioxobenzo[d]imidazole-1-yl)ethanone
0.02
-
pH 7.4, 37°C Streptococcus agalactiae 3-cyclohexyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
0.02
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxo-1H-benzo[d]imidazol-1-yl)butan-1-one
0.021
-
pH 7.4, 37°C Streptococcus agalactiae methyl-3-(3-phenylpropanoyl)-2,3-dihydro-2-thioxobenzo[d]oxazole-5-carboxylate
0.024
-
pH 7.4, 37°C Streptococcus agalactiae 3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
0.024
-
pH 7.4, 37°C Streptococcus agalactiae N-(3-phenylpropionyl)benzoxazole-2-thione
0.025
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxobenzo[d]oxazol-3(2H)-yl)decan-1-one
0.026
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxo-1H-benzo[d]imidazol-1-yl)propan-1one
0.029
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxo-1H-benzo[d]imidazol-1-yl)-3-phenylpropan-1-one
0.029
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxobenzo[d]oxazol-3(2H)-yl)hexan-1-one
0.042
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
0.048
-
pH 7.4, 37°C Streptococcus agalactiae 1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
0.062
-
pH 7.4, 37°C Streptococcus agalactiae 2-phenoxy-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
0.069
-
pH 7.4, 37°C Streptococcus agalactiae 2-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
0.07
-
pH 7.4, 37°C Streptococcus agalactiae (3-chlorophenyl)(2-thioxo-1H-benzo[d]imidazol-1-yl)methanone
0.556
-
pH 7.4, 37°C Streptococcus agalactiae benzyl 2-thioxobenzo[d]oxazol-3(2H)-carboxylate
1.45
-
pH 7.4, 37°C Streptococcus agalactiae 3-acetylbenzo[d]oxazol-2(3H)-one
1.86
-
pH 7.4, 37°C Streptococcus agalactiae 1,3-dihydro-2H-benzimidazole-2-thione
2.54
-
pH 7.4, 37°C Streptococcus agalactiae 1,3-benzoxazole-2(3H)-thione

General Information

General Information Comment Organism
physiological function hyaluronan lyases degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread Streptococcus agalactiae