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Literature summary for 3.5.2.6 extracted from

  • Zhang, Y.L.; Yang, K.W.; Zhou, Y.J.; LaCuran, A.E.; Oelschlaeger, P.; Crowder, M.W.
    Diaryl-substituted azolylthioacetamides: Inhibitor discovery of New Delhi metallo-beta-lactamase-1 (NDM-1) (2014), ChemMedChem, 9, 2445-2448.
    View publication on PubMed
Search for more literature for 3.5.2.6

Inhibitors

Inhibitors Comment Organism Structure
2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide
-
 Aeromonas veronii
2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide
-
 Bacteroides fragilis
2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide
-
 Stenotrophomonas maltophilia
2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]-N-phenylacetamide
-
 Aeromonas veronii
2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]-N-phenylacetamide
-
 Stenotrophomonas maltophilia
2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide
-
 Aeromonas veronii
2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide
-
 Bacteroides fragilis
2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide
-
 Stenotrophomonas maltophilia
additional information development of diaryl-substituted azolylthioacetamides as metallo-beta-lactamase-1 enzyme inhibitors, overview no inhibition by N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide, N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide, N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide, N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide, N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide, and N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide, poor inhibition by N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide, 2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]-N-phenylacetamide, N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide, N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide, N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide, and N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide; development of eighteen diaryl-substituted azolylthioacetamides as metallo-beta-lactamase enzyme inhibitors, overview. No inhibition by N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide, N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide, N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide, and N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide. Docking studies reveal that the azolylthioacetamides, which have the broadest inhibitory activity, coordinate to the ZnII ion(s) preferentially via the triazole moiety, while other moieties interact mostly with the conserved active site residues Aeromonas veronii
additional information development of diaryl-substituted azolylthioacetamides as metallo-beta-lactamase-1 enzyme inhibitors, overview Bacteroides fragilis
additional information development of eighteen diaryl-substituted azolylthioacetamides as New Delhi metallo-beta-lactamase-1 enzyme inhibitors, overview Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Bacteroides fragilis
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Bacteroides fragilis
N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Bacteroides fragilis
N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia
N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Aeromonas veronii
N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide
-
 Stenotrophomonas maltophilia

Organism

Organism UniProt Comment Textmining
Aeromonas veronii
-
-
-
Aeromonas veronii O31272
-
-
Bacteroides fragilis P25910
-
-
Stenotrophomonas maltophilia E9RIT0
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
cefazolin + H2O
-
 Aeromonas veronii (2R)-2-[(R)-carboxy[2-(1H-tetrazol-1-yl)acetamido]methyl]-5-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?
cefazolin + H2O
-
 Bacteroides fragilis (2R)-2-[(R)-carboxy[2-(1H-tetrazol-1-yl)acetamido]methyl]-5-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?
cefazolin + H2O
-
 Stenotrophomonas maltophilia (2R)-2-[(R)-carboxy[2-(1H-tetrazol-1-yl)acetamido]methyl]-5-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?
imipenem + H2O
-
 Aeromonas veronii (5R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-([2-[(iminomethyl)amino]ethyl]sulfanyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid
-
 ?
imipenem + H2O
-
 Bacteroides fragilis (5R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-([2-[(iminomethyl)amino]ethyl]sulfanyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid
-
 ?
imipenem + H2O
-
 Stenotrophomonas maltophilia (5R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-([2-[(iminomethyl)amino]ethyl]sulfanyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid
-
 ?

Synonyms

Synonyms Comment Organism
CcrA
-
 Bacteroides fragilis
ImiS
-
 Aeromonas veronii
NDM-1
-
 Aeromonas veronii
NDM-1
-
 Stenotrophomonas maltophilia
New Delhi MbetaL-1
-
 Stenotrophomonas maltophilia
New Delhi metallo-beta-lactamase-1
-
 Aeromonas veronii
New Delhi metallo-beta-lactamase-1
-
 Stenotrophomonas maltophilia

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000073
-
 2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00023
-
 N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.00025
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00025
-
 N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.0003
-
 2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Bacteroides fragilis
0.00033
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00034
-
 2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00034
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00035
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.00038
-
 N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00039
-
 N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00042
-
 N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.00043
-
 2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Aeromonas veronii
0.00043
-
 N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00051
-
 2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00051
-
 N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00054
-
 N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.0006
-
 2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Aeromonas veronii
0.00064
-
 2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Aeromonas veronii
0.00065
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00075
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.00081
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.00082
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.00086
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.001
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.0011
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0012
-
 N-phenyl-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0013
-
 N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0014
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.0018
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Stenotrophomonas maltophilia
0.0022
-
 2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Aeromonas veronii
0.0033
-
 2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Aeromonas veronii
0.0043
-
 N-phenyl-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0053
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0056
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0061
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.0063
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Bacteroides fragilis
0.0068
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.007
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Bacteroides fragilis
0.0085
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetamide pH and temperature not specified in the publication Bacteroides fragilis
0.015
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.045
-
 N-(1,3-benzothiazol-2-yl)-2-[[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide pH and temperature not specified in the publication Aeromonas veronii
0.052
-
 2-[[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-phenylacetamide pH and temperature not specified in the publication Bacteroides fragilis

General Information

General Information Comment Organism
evolution the enzyme is a metallo-beta-lactamase of subgroup B1a Bacteroides fragilis
evolution the enzyme is a metallo-beta-lactamase of subgroup B1b Aeromonas veronii
evolution the enzyme is a metallo-beta-lactamase of subgroup B2 Aeromonas veronii
evolution the enzyme is a metallo-beta-lactamase of subgroup B3 Stenotrophomonas maltophilia