BRENDA - Enzyme Database
show all sequences of 6.3.2.9

Design and synthesis of novel N-benzylidenesulfonohydrazide inhibitors of MurC and MurD as potential antibacterial agents

Frlan, R.; Kovac, A.; Blanot, D.; Gobec, S.; Pecar, S.; Obreza, A.; Molecules 13, 11-30 (2008) View publication on PubMedView publication on EuropePMC

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 2-nitrobenzenesulfonate
71% inhibition at 0.05 mM
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 3-nitrobenzenesulfonate
70% inhibition at 0.05 mM
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 4-nitrobenzenesulfonate
-
Escherichia coli
2-([2-(naphthalen-2-ylsulfonyl)hydrazono]methyl)phenyl 2-(benzo[d][1,3]dioxol-5-yl)acetate
49% inhibition at 0.10 mM
Escherichia coli
2-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
Escherichia coli
3-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
Escherichia coli
4-cyano-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
78% inhibition at 0.05 mM
Escherichia coli
benzylidene rhodanines
possess MurC inhibitory activity in the low micromolar range
Escherichia coli
additional information
design and synthesis of N-benzylidenesulfonohydrazide inhibitors of MurC as antibacterial agents
Escherichia coli
N'-((2-[(2-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
Escherichia coli
N'-((2-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
70% inhibition at 0.05 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(2-fluorophenyl)methanesulfonohydrazide
39% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(phenyl)methanesulfonohydrazide
58% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-nitrobenzenesulfonohydrazide
86% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-3-nitrobenzenesulfonohydrazide
74% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)[4-(trifluoromethyl)phenyl]methanesulfonohydrazide
57% inhibition at 0.10 mM
Escherichia coli
N'-((3-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
61% inhibition at 0.05 mM
Escherichia coli
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide
-
Escherichia coli
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
-
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-naphthamide
19% inhibition at 0.01 mM
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-nitrobenzamide
-
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide
78% inhibition at 0.10 mM
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
81% inhibition at 0.05 mM
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
56% inhibition at 0.10 mM
Escherichia coli
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Mg2+
-
Escherichia coli
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
ATP + UDP-N-acetylmuramyl-L-alanine + D-glutamate
Escherichia coli
-
ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Escherichia coli
-
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
ATP + UDP-N-acetylmuramyl-L-alanine + D-glutamate
-
694288
Escherichia coli
ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
MurD
-
Escherichia coli
UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase
-
Escherichia coli
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Escherichia coli
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Escherichia coli
Cofactor
Cofactor
Commentary
Organism
Structure
ATP
-
Escherichia coli
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.03
-
pH 8.0, 37°C
Escherichia coli
3-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
0.045
-
pH 8.0, 37°C
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-nitrobenzamide
0.055
-
pH 8.0, 37°C
Escherichia coli
2-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
0.062
-
pH 8.0, 37°C
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
0.07
-
pH 8.0, 37°C
Escherichia coli
N'-((2-[(2-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
0.074
-
pH 8.0, 37°C
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 4-nitrobenzenesulfonate
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
ATP
-
Escherichia coli
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.03
-
pH 8.0, 37°C
Escherichia coli
3-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
0.045
-
pH 8.0, 37°C
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-nitrobenzamide
0.055
-
pH 8.0, 37°C
Escherichia coli
2-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
0.062
-
pH 8.0, 37°C
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
0.07
-
pH 8.0, 37°C
Escherichia coli
N'-((2-[(2-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
0.074
-
pH 8.0, 37°C
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 4-nitrobenzenesulfonate
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 2-nitrobenzenesulfonate
71% inhibition at 0.05 mM
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 3-nitrobenzenesulfonate
70% inhibition at 0.05 mM
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 4-nitrobenzenesulfonate
-
Escherichia coli
2-([2-(naphthalen-2-ylsulfonyl)hydrazono]methyl)phenyl 2-(benzo[d][1,3]dioxol-5-yl)acetate
49% inhibition at 0.10 mM
Escherichia coli
2-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
Escherichia coli
3-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
Escherichia coli
4-cyano-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
78% inhibition at 0.05 mM
Escherichia coli
benzylidene rhodanines
possess MurC inhibitory activity in the low micromolar range
Escherichia coli
additional information
design and synthesis of N-benzylidenesulfonohydrazide inhibitors of MurC as antibacterial agents
Escherichia coli
N'-((2-[(2-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
Escherichia coli
N'-((2-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
70% inhibition at 0.05 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(2-fluorophenyl)methanesulfonohydrazide
39% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(phenyl)methanesulfonohydrazide
58% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-nitrobenzenesulfonohydrazide
86% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-3-nitrobenzenesulfonohydrazide
74% inhibition at 0.10 mM
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)[4-(trifluoromethyl)phenyl]methanesulfonohydrazide
57% inhibition at 0.10 mM
Escherichia coli
N'-((3-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
61% inhibition at 0.05 mM
Escherichia coli
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide
-
Escherichia coli
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
-
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-naphthamide
19% inhibition at 0.01 mM
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-nitrobenzamide
-
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide
78% inhibition at 0.10 mM
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
81% inhibition at 0.05 mM
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
56% inhibition at 0.10 mM
Escherichia coli
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Mg2+
-
Escherichia coli
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
ATP + UDP-N-acetylmuramyl-L-alanine + D-glutamate
Escherichia coli
-
ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
ATP + UDP-N-acetylmuramyl-L-alanine + D-glutamate
-
694288
Escherichia coli
ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Escherichia coli
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Escherichia coli
Other publictions for EC 6.3.2.9
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
746203
Sink
Crystallographic study of pept ...
Escherichia coli
PLoS ONE
11
e0152075
2016
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715974
Tomasic
Virtual screening for potentia ...
Escherichia coli
J. Mol. Model.
18
1063-1072
2012
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714902
Sosic
Second-generation sulfonamide ...
Escherichia coli
Eur. J. Med. Chem.
46
2880-2894
2011
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4
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714905
Tomasic
Novel 2-thioxothiazolidin-4-on ...
Escherichia coli
Eur. J. Med. Chem.
46
3964-3975
2011
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715866
Tomasic
Structure-based design of a ne ...
Escherichia coli
J. Med. Chem.
54
4600-4610
2011
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5
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7
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714367
Patin
Purification and biochemical c ...
Staphylococcus aureus
Biochimie
92
1793-1800
2010
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3
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715722
Umamaheswari
-
Virtual screening for potentia ...
Leptospira interrogans
J. Chem. Biol.
13
175-187
2010
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1
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715847
Zidar
Discovery of novel 5-benzylide ...
Escherichia coli
J. Med. Chem.
53
6584-6594
2010
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702636
Turk
Discovery of new inhibitors of ...
Escherichia coli
Bioorg. Med. Chem.
17
1884-1889
2009
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704728
Kristan
New high-throughput fluorimetr ...
Escherichia coli
J. Biomol. Screen.
14
412-418
2009
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1
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705031
Simcic
NMR and molecular dynamics stu ...
Escherichia coli
J. Med. Chem.
52
2899-2908
2009
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705227
Perdih
Binding free energy calculatio ...
Escherichia coli
J. Mol. Model.
15
983-996
2009
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690835
Thakur
Ability of PknA, a mycobacteri ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Ra / ATCC 25177
Biochem. J.
415
27-33
2008
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