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Literature summary for 2.3.1.180 extracted from

  • Alhamadsheh, M.; Waters, N.; Sachdeva, S.; Lee, P.; Reynolds, K.
    Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors (2008), Bioorg. Med. Chem. Lett., 18, 6402-6405 .
    View publication on PubMed
Search for more literature for 2.3.1.180

Inhibitors

Inhibitors Comment Organism Structure
2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
-
 Escherichia coli
2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
-
 Plasmodium falciparum
2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
-
 Escherichia coli
2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
-
 Plasmodium falciparum
2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2-(benzenesulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2-(benzenesulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2-(methanesulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2-(methanesulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
-
 Escherichia coli
3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
-
 Plasmodium falciparum
3-(2-phenylethyl)-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
3-benzyl-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
3-[(4-phenoxyphenyl)methyl]-1,3-thiazolidin-2-one
-
 Escherichia coli
3-[(4-phenoxyphenyl)methyl]-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1,3-thiazolidin-2-one
-
 Escherichia coli
3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1,3-thiazolidine-2-thione
-
 Escherichia coli
3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
additional information 2-tosylnaphthalene-1,4-diol analogues are reversible inhibitors (10-20 nM) of Escherichia coli FabH. The sulfonyl group and naphthalene-1,4 diol are required for activity against all enzymes but the toluene portion can be significantly altered. Inhibitors are also effective against the Mycobacterium tuberculosis (EC 2.3.1.301) and Plasmodium falciparum FabH enzymes; synthesis and evalutation of cyclic sulfones. The compounds are selectively active against Escherichia coli FabH, but not Mycobacterium tuberculosis FabH (EC 2.3.1.301) or Plasmodium falciparum KASIII Escherichia coli
additional information 2-tosylnaphthalene-1,4-diol analogues are reversible inhibitors of Plasmodium falciparum FabH. The sulfonyl group and naphthalene-1,4 diol are required for activity against all enzymes but the toluene portion can be significantly altered. Inhibitors are also effective against the Mycobacterium tuberculosis (EC 2.3.1.301) and Escherichia coli FabH enzymes Plasmodium falciparum
[4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
-
 Escherichia coli
[4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
-
 Plasmodium falciparum

Organism

Organism UniProt Comment Textmining
Escherichia coli P0A6R0
-
-
Plasmodium falciparum
-
-
-

Synonyms

Synonyms Comment Organism
FabH
-
 Plasmodium falciparum
FabH
-
 Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00000212
-
 pH 7.4, 23°C Escherichia coli 2-(benzenesulfonyl)naphthalene-1,4-diol
0.0000088
-
 pH 7.4, 23°C Escherichia coli 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
0.0000097
-
 pH 7.4, 23°C Escherichia coli 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
0.0000118
-
 pH 7.4, 23°C Escherichia coli [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
0.0000136
-
 pH 7.4, 23°C Escherichia coli 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
0.0000154
-
 pH 7.4, 23°C Escherichia coli 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
0.0000275
-
 pH 7.4, 23°C Plasmodium falciparum 2-(methanesulfonyl)naphthalene-1,4-diol
0.0000296
-
 pH 7.4, 23°C Plasmodium falciparum [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
0.0000465
-
 pH 7.4, 23°C Plasmodium falciparum 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
0.0000726
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
0.0000736
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
0.0000873
-
 pH 7.4, 23°C Escherichia coli 2-(methanesulfonyl)naphthalene-1,4-diol
0.0000965
-
 pH 7.4, 23°C Escherichia coli 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
0.0001124
-
 pH 7.4, 23°C Escherichia coli 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
0.0001287
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
0.0001872
-
 pH 7.4, 23°C Escherichia coli 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
0.0002787
-
 pH 7.4, 23°C Plasmodium falciparum 2-(benzenesulfonyl)naphthalene-1,4-diol
0.0003411
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
0.000393
-
 pH 7.4, 23°C Plasmodium falciparum 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
0.0009
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-[(4-phenoxyphenyl)methyl]-1lambda6,3-thiazolidine-1,1,2-trione
0.0011
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-benzyl-1lambda6,3-thiazolidine-1,1,2-trione
0.0019
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-(2-phenylethyl)-1lambda6,3-thiazolidine-1,1,2-trione
0.0024
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1lambda6,3-thiazolidine-1,1,2-trione
0.0109
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-[(4-phenoxyphenyl)methyl]-1,3-thiazolidin-2-one
0.0144
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1,3-thiazolidin-2-one
0.0177
-
 pH not specified in the publication, temperature not specified in the publication Escherichia coli 3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1,3-thiazolidine-2-thione