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

BRENDA support

Literature summary 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

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.180 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
-
 Escherichia coli
2.3.1.180 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
-
 Plasmodium falciparum
2.3.1.180 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 2-(benzenesulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(benzenesulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 2-(methanesulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(methanesulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
-
 Escherichia coli
2.3.1.180 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
-
 Plasmodium falciparum
2.3.1.180 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
-
 Escherichia coli
2.3.1.180 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
-
 Plasmodium falciparum
2.3.1.180 3-(2-phenylethyl)-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
2.3.1.180 3-benzyl-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
2.3.1.180 3-[(4-phenoxyphenyl)methyl]-1,3-thiazolidin-2-one
-
 Escherichia coli
2.3.1.180 3-[(4-phenoxyphenyl)methyl]-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
2.3.1.180 3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1,3-thiazolidin-2-one
-
 Escherichia coli
2.3.1.180 3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1,3-thiazolidine-2-thione
-
 Escherichia coli
2.3.1.180 3-[[4-(4-cyclopentylphenoxy)phenyl]methyl]-1lambda6,3-thiazolidine-1,1,2-trione
-
 Escherichia coli
2.3.1.180 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
2.3.1.180 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
2.3.1.180 [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
-
 Escherichia coli
2.3.1.180 [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
-
 Plasmodium falciparum
2.3.1.301 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
-
 Mycobacterium tuberculosis
2.3.1.301 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 2-(benzenesulfonyl)naphthalene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 2-(methanesulfonyl)naphthalene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
-
 Mycobacterium tuberculosis
2.3.1.301 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
-
 Mycobacterium tuberculosis
2.3.1.301 additional information 2-tosylnaphthalene-1,4-diol analogues are reversible inhibitors (30 nM-5 microM) of the Mycobacterium tuberculosis and Plasmodium falciparum FabH enzymes. 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 Escherichia coli FabH, EC 2.3.1.180 Mycobacterium tuberculosis
2.3.1.301 [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
-
 Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.180 Escherichia coli P0A6R0
-
-
2.3.1.180 Plasmodium falciparum
-
-
-
2.3.1.301 Mycobacterium tuberculosis P9WNG3
-
-
2.3.1.301 Mycobacterium tuberculosis H37Rv P9WNG3
-
-

Synonyms

EC Number Synonyms Comment Organism
2.3.1.180 FabH
-
 Plasmodium falciparum
2.3.1.180 FabH
-
 Escherichia coli
2.3.1.301 FabH
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.3.1.180 0.00000212
-
 pH 7.4, 23°C Escherichia coli 2-(benzenesulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000088
-
 pH 7.4, 23°C Escherichia coli 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000097
-
 pH 7.4, 23°C Escherichia coli 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000118
-
 pH 7.4, 23°C Escherichia coli [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
2.3.1.180 0.0000136
-
 pH 7.4, 23°C Escherichia coli 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000154
-
 pH 7.4, 23°C Escherichia coli 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000275
-
 pH 7.4, 23°C Plasmodium falciparum 2-(methanesulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000296
-
 pH 7.4, 23°C Plasmodium falciparum [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
2.3.1.180 0.0000465
-
 pH 7.4, 23°C Plasmodium falciparum 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
2.3.1.180 0.0000726
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000736
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000873
-
 pH 7.4, 23°C Escherichia coli 2-(methanesulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0000965
-
 pH 7.4, 23°C Escherichia coli 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
2.3.1.180 0.0001124
-
 pH 7.4, 23°C Escherichia coli 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
2.3.1.180 0.0001287
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0001872
-
 pH 7.4, 23°C Escherichia coli 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
2.3.1.180 0.0002787
-
 pH 7.4, 23°C Plasmodium falciparum 2-(benzenesulfonyl)naphthalene-1,4-diol
2.3.1.180 0.0003411
-
 pH 7.4, 23°C Plasmodium falciparum 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol
2.3.1.180 0.000393
-
 pH 7.4, 23°C Plasmodium falciparum 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
2.3.1.180 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
2.3.1.180 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
2.3.1.180 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
2.3.1.180 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
2.3.1.180 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
2.3.1.180 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
2.3.1.180 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
2.3.1.301 0.0000002
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-dione
2.3.1.301 0.00000061
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(4-methylbenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.301 0.0000015
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(naphthalene-2-sulfonyl)naphthalene-1,4-diol
2.3.1.301 0.0000028
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(benzenesulfonyl)naphthalene-1,4-diol
2.3.1.301 0.0000031
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(4-propylbenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.301 0.0000035
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(methanesulfonyl)naphthalene-1,4-diol
2.3.1.301 0.0000035
-
 pH 7.4, 23°C Mycobacterium tuberculosis 3-(1,4-dihydroxynaphthalene-2-sulfonyl)propanoic acid
2.3.1.301 0.0000036
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(4-chlorobenzene-1-sulfonyl)naphthalene-1,4-diol
2.3.1.301 0.0000038
-
 pH 7.4, 23°C Mycobacterium tuberculosis [4-(1,4-dihydroxynaphthalene-2-sulfonyl)phenyl]carbamic acid
2.3.1.301 0.0000085
-
 pH 7.4, 23°C Mycobacterium tuberculosis 2-(4-methylbenzene-1-sulfonyl)anthracene-1,4-diol