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Literature summary for 1.1.1.21 extracted from

  • Hao, X.; Qi, G.; Ma, H.; Zhu, C.; Han, Z.
    Novel 2-phenoxypyrido[3,2-b]pyrazin-3(4H)-one derivatives as potent and selective aldose reductase inhibitors with antioxidant activity (2019), J. Enzyme Inhib. Med. Chem., 34, 1368-1372 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
molecular docking of inhibitor 6-chloro-3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2-oxo-3-(3,4,5-trihydroxyphenoxy)-1,8-naphthyridine-1(2H)-carboxylic acid 21.7fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
2-oxo-3-(3,4,5-trimethoxyphenoxy)-1,8-naphthyridine-1(2H)-carboxylic acid 20.8fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
2-oxo-3-phenoxy-1,8-naphthyridine-1(2H)-carboxylic acid 27fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3,4-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 16.9fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3,4-dimethoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 17.6fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3,5-dihydroxy-4-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 25.8fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 20.8fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3,5-dimethoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 21.5fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3-hydroxy-4,5-dimethoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 31.6fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3-hydroxy-4-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 19.3fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(3-hydroxy-5-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 15.1fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(4-hydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 15.9fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
3-(4-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 20fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
6-bromo-3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 19.8fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
6-chloro-3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid 18.4fold selectivity for AKR1B1 over AKR1A1 Homo sapiens
epalrestat 55.7fold selectivity for isoform AKR1B1 over AKR1A1 Homo sapiens
additional information synthesis of 2-phenoxypyrido[3,2-b]pyrazin-3(4H)-one derivatives.The combination of phenolic 3,5-dihydroxyl in the C2-phenoxy group and C7-halogen (Cl or Br) in the core structure largely increases the AKR1B1 inhibitory activity, and the 3,5-dihydroxyl substituent contributes greatly to the activity enhancement of antioxidation when comparing all the phenolic hydroxyl derivatives Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P15121
-
-

Synonyms

Synonyms Comment Organism
AKR1B1
-
Homo sapiens
ALR2
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000023
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 6-chloro-3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.000056
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 6-bromo-3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.000087
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3,5-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.000089
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens epalrestat
0.00012
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(4-hydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00031
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3,4-dihydroxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00086
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 2-oxo-3-(3,4,5-trihydroxyphenoxy)-1,8-naphthyridine-1(2H)-carboxylic acid
0.00236
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3,5-dihydroxy-4-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.0025
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3-hydroxy-4-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00268
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(4-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00285
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3-hydroxy-5-methoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.0043
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3,5-dimethoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00453
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3-hydroxy-4,5-dimethoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00568
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(3,4-dimethoxyphenoxy)-2-oxo-1,8-naphthyridine-1(2H)-carboxylic acid
0.00757
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 2-oxo-3-(3,4,5-trimethoxyphenoxy)-1,8-naphthyridine-1(2H)-carboxylic acid
0.00857
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens 2-oxo-3-phenoxy-1,8-naphthyridine-1(2H)-carboxylic acid