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Literature summary for 6.3.2.8 extracted from

  • Frlan, R.; Kovac, A.; Blanot, D.; Gobec, S.; Pecar, S.; Obreza, A.
    Design and synthesis of novel N-benzylidenesulfonohydrazide inhibitors of MurC and MurD as potential antibacterial agents (2008), Molecules, 13, 11-30.
    View publication on PubMedView publication on EuropePMC

Inhibitors

Inhibitors Comment Organism Structure
(5Z)-5-([2-[(4-chlorobenzyl)sulfanyl]-5-nitrophenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
-
Escherichia coli
(5Z)-5-([4-[(E)-2-phenylethenyl]phenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
-
Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 2-nitrobenzenesulfonate 55% inhibition at 0.05 mM Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 3-nitrobenzenesulfonate 65% inhibition at 0.05 mM Escherichia coli
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 4-nitrobenzenesulfonate 75% inhibition at 0.10 mM Escherichia coli
2-([2-(naphthalen-2-ylsulfonyl)hydrazono]methyl)phenyl 2-(benzo[d][1,3]dioxol-5-yl)acetate 57% inhibition at 0.10 mM Escherichia coli
2-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide 41% inhibition at 0.10 mM 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 91% 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 30% inhibition at 0.10 mM Escherichia coli
N'-((2-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide 36% inhibition at 0.05 mM Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(2-fluorophenyl)methanesulfonohydrazide 59% inhibition at 0.10 mM Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(phenyl)methanesulfonohydrazide complete inhibition at 0.10 mM Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide 36% inhibition at 0.10 mM Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-nitrobenzenesulfonohydrazide 95% inhibition at 0.01 mM Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-3-nitrobenzenesulfonohydrazide
-
Escherichia coli
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)[4-(trifluoromethyl)phenyl]methanesulfonohydrazide
-
Escherichia coli
N'-((3-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide 58% inhibition at 0.05 mM Escherichia coli
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide 51% inhibition at 0.10 mM Escherichia coli
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
-
Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-naphthamide
-
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 72% inhibition at 0.10 mM Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide 71% inhibition at 0.05 mM Escherichia coli
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide 97% inhibition at 0.10 mM Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+
-
Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + UDP-N-acetylmuramate + L-alanine Escherichia coli
-
ADP + phosphate + UDP-N-acetylmuramoyl-L-alanine
-
?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + UDP-N-acetylmuramate + L-alanine
-
Escherichia coli ADP + phosphate + UDP-N-acetylmuramoyl-L-alanine
-
?

Synonyms

Synonyms Comment Organism
MurC
-
Escherichia coli
UDP-MurNAc:L-Ala ligase
-
Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
assay at Escherichia coli

Cofactor

Cofactor Comment Organism Structure
ATP
-
Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.018
-
pH 8.0, 37°C Escherichia coli (5Z)-5-([4-[(E)-2-phenylethenyl]phenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
0.027
-
pH 8.0, 37°C Escherichia coli N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
0.027
-
pH 8.0, 37°C Escherichia coli (5Z)-5-([2-[(4-chlorobenzyl)sulfanyl]-5-nitrophenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
0.03
-
pH 8.0, 37°C Escherichia coli 3-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
0.031
-
pH 8.0, 37°C Escherichia coli N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-naphthamide
0.051
-
pH 8.0, 37°C Escherichia coli N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-nitrobenzamide