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Literature summary extracted from

  • Lu, W.; Baig, I.A.; Sun, H.J.; Cui, C.J.; Guo, R.; Jung, I.P.; Wang, D.; Dong, M.; Yoon, M.Y.; Wang, J.G.
    Synthesis, crystal structure and biological evaluation of substituted quinazolinone benzoates as novel antituberculosis agents targeting acetohydroxyacid synthase (2015), Eur. J. Med. Chem., 94, 298-305 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.2.1.6 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-(trifluoromethyl)benzoate 30% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-chlorobenzoate 42.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-fluorobenzoate 72% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-methoxybenzoate 28% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl benzoate 26% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl 3-(trifluoromethyl)benzoate 73.2% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl 3-chlorobenzoate 23.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 2-(3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl 3-nitrobenzoate 94% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-m-tolylquinazolin-3(4H)-yl 3-fluorobenzoate 9.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-m-tolylquinazolin-3(4H)-yl 3-methylbenzoate 10.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-m-tolylquinazolin-3(4H)-yl 4-chlorobenzoate no inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-m-tolylquinazolin-3(4H)-yl 4-methylbenzoate 33% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-m-tolylquinazolin-3(4H)-yl benzoate 40.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-m-tolylquinazolin-3(4H)-yl-3-(trifluoromethyl)benzoate 9.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-o-tolylquinazolin-3(4H)-yl 3-fluorobenzoate 30% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 2-methylbenzoate 16.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 3-chlorobenzoate 80.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 3-fluorobenzoate 26% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 3-methoxybenzoate 27% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 3-methylbenzoate 4% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 3-nitrobenzoate 91.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 4-chlorobenzoate 7.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl 4-methylbenzoate 18% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 4-oxo-2-phenylquinazolin-3(4H)-yl benzoate 20.5% inhibition at 0.1 mM Mycobacterium tuberculosis
2.2.1.6 isoniazid
-
 Mycobacterium tuberculosis
2.2.1.6 Rifampin
-
 Mycobacterium tuberculosis
2.2.1.6 sulfometuron methyl
-
 Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.2.1.6 Mg2+ 10 mM used in assay conditions Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.2.1.6 2 pyruvate Mycobacterium tuberculosis
-
 2-acetolactate + CO2
-
 ?
2.2.1.6 2 pyruvate Mycobacterium tuberculosis H37Rv
-
 2-acetolactate + CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.2.1.6 Mycobacterium tuberculosis
-
-
-
2.2.1.6 Mycobacterium tuberculosis H37Rv
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.2.1.6 2 pyruvate
-
 Mycobacterium tuberculosis 2-acetolactate + CO2
-
 ?
2.2.1.6 2 pyruvate
-
 Mycobacterium tuberculosis H37Rv 2-acetolactate + CO2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.2.1.6 acetohydroxyacid synthase
-
 Mycobacterium tuberculosis
2.2.1.6 acetolactate synthase
-
 Mycobacterium tuberculosis
2.2.1.6 AHAS
-
 Mycobacterium tuberculosis
2.2.1.6 ALS
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.2.1.6 0.00479
-
 at pH 7.5 and 37°C Mycobacterium tuberculosis sulfometuron methyl
2.2.1.6 0.0065
-
 at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-fluorobenzoate
2.2.1.6 0.00874
-
 at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl 3-nitrobenzoate
2.2.1.6 0.00957
-
 at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl 3-(trifluoromethyl)benzoate
2.2.1.6 0.00968
-
 at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 3-nitrobenzoate
2.2.1.6 0.01208
-
 at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 3-chlorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-(trifluoromethyl)benzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-chlorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl 3-methoxybenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-fluorophenyl)-4-oxoquinazolin-3(4H)-yl benzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 2-(3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl 3-chlorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-m-tolylquinazolin-3(4H)-yl 3-fluorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-m-tolylquinazolin-3(4H)-yl 3-methylbenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-m-tolylquinazolin-3(4H)-yl 4-chlorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-m-tolylquinazolin-3(4H)-yl 4-methylbenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-m-tolylquinazolin-3(4H)-yl benzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-m-tolylquinazolin-3(4H)-yl-3-(trifluoromethyl)benzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-o-tolylquinazolin-3(4H)-yl 3-fluorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 2-methylbenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 3-fluorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 3-methoxybenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 3-methylbenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 4-chlorobenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl 4-methylbenzoate
2.2.1.6 0.1
-
 IC50 above 0.1 mM, at pH 7.5 and 37°C Mycobacterium tuberculosis 4-oxo-2-phenylquinazolin-3(4H)-yl benzoate