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Literature summary extracted from

  • Hussain, S.; Parveen, S.; Hao, X.; Zhang, S.; Wang, W.; Qin, X.; Yang, Y.; Chen, X.; Zhu, S.; Zhu, C.; Ma, B.
    Structure-activity relationships studies of quinoxalinone derivatives as aldose reductase inhibitors (2014), Eur. J. Med. Chem., 80, 383-392.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.2 1-(4-nitrobenzyl)-3-(4-(2-morpholinoethyl) piperazin-1-yl)quinoxalin-2(1H)-one 23% inhibition Rattus norvegicus
1.1.1.2 1-(4-nitrobenzyl)-3-(4-(3-(trifluoromethyl) phenyl)piperazin-1-yl) quinoxalin-2(1H)-one 43% inhibition Rattus norvegicus
1.1.1.2 1-(4-nitrobenzyl)-3-(4-(4-methoxyphenyl) piperazin-1-yl)quinoxalin-2(1H)-one 26% inhibition Rattus norvegicus
1.1.1.2 1-(4-nitrobenzyl)-3-(4-(pyrazin-2-yl) piperazin-1-yl)quinoxalin-2(1H)-one 24% inhibition Rattus norvegicus
1.1.1.2 1-(4-nitrobenzyl)-3-styrylquinoxalin-2(1H)-one 30% inhibition Rattus norvegicus
1.1.1.2 2-(2-oxo-3-phenethylquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(3-(2,4-difluorophenylamino)-6-nitro-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(3-(3-(tert-butylamino)-3-oxoprop-1-en-1-yl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(3-(4-(4-methoxyphenyl) piperazin-1-yl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(3-(4-fluorophenethyl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(3-(4-fluorostyryl)-6-nitro-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(6-chloro-3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
 Rattus norvegicus
1.1.1.2 2-(7-chloro-2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid
-
 Rattus norvegicus
1.1.1.2 3-(4-fluorostyryl)-1-(4-nitrobenzyl) quinoxalin-2(1H)-one 24% inhibition Rattus norvegicus
1.1.1.2 3-(benzo[b] thiophen-3-yl)-1-(4-nitrobenzyl)quinoxalin-2(1H)-one 32% inhibition Rattus norvegicus
1.1.1.2 additional information structure-activity relationships study of quinoxalinone derivatives as aldose reductase inhibitors. Among them, N1-acetate derivatives have significant activity, molecular modeling and docking, overview. Both C3-phenethyl and C6-NO2 groups play an important role in enhancing the activity and selectivity of the quinoxalinone based inhibitors Rattus norvegicus
1.1.1.2 N-(tert-butyl)-3-(4-(4-nitrobenzyl)-3-oxo-3, 4-dihydroquinoxalin-2-yl) acryl amide 36% inhibition Rattus norvegicus
1.1.1.21 1-(4-nitrobenzyl)-3-(4-(2-morpholinoethyl)piperazin-1-yl)quinoxalin-2(1H)-one
-
 Rattus norvegicus
1.1.1.21 1-(4-nitrobenzyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)quinoxalin-2(1H)-one
-
 Rattus norvegicus
1.1.1.21 1-(4-nitrobenzyl)-3-(4-(pyrazin-2-yl)piperazin-1-yl)quinoxalin-2(1H)-one}
-
 Rattus norvegicus
1.1.1.21 1-(4-nitrobenzyl)-3-styryl-quinoxalin-2(1H)-one
-
 Rattus norvegicus
1.1.1.21 2-(2-oxo-3-phenethylquinoxalin-1(2H)-yl)acetic acid 22% inhibition Rattus norvegicus
1.1.1.21 2-(2-oxo-3-styrylquinoxalin-1(2H)-yl)acetic acid 32% inhibition Rattus norvegicus
1.1.1.21 2-(3-(2,4-difluorophenylamino)-6-nitro-2-oxoquinoxalin-1(2H)-yl) acetic acid} 41% inhibition Rattus norvegicus
1.1.1.21 2-(3-(3-(tert-butylamino)-3-oxoprop-1-en-1-yl)-2-oxoquinoxalin-1(2H)-yl)acetic acid 25% inhibition Rattus norvegicus
1.1.1.21 2-(3-(4-(4-methoxyphenyl) piperazin-1-yl)-2-oxoquinoxalin-1(2H)-yl)acetic acid 48% inhibition Rattus norvegicus
1.1.1.21 2-(3-(4-fluorophenethyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid 40% inhibition Rattus norvegicus
1.1.1.21 2-(3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl)acetic acid 47% inhibition Rattus norvegicus
1.1.1.21 2-(3-(4-fluorostyryl)-6-nitro-2-oxoquinoxalin-1(2H)-yl)acetic acid} 25% inhibition Rattus norvegicus
1.1.1.21 2-(6-chloro-3-(4-fluoro-styryl)-2-oxoquinoxalin-1(2H)-yl)acetic acid 25% inhibition Rattus norvegicus
1.1.1.21 2-(7-chloro-2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid} 35% inhibition Rattus norvegicus
1.1.1.21 3-(4-fluorostyryl)-1-(4-nitrobenzyl)quinoxalin-2(1H)-one
-
 Rattus norvegicus
1.1.1.21 3-(benzo[b] thiophen-3-yl)-1-(4-nitrobenzylquinoxalin-2(1H)-one
-
 Rattus norvegicus
1.1.1.21 additional information structure-activity relationships study of quinoxalinone derivatives as aldose reductase inhibitors. Among them, N1-acetate derivatives have significant activity, molecular modeling and docking, overview. Both C3-phenethyl and C6-NO2 groups play an important role in enhancing the activity and selectivity of the quinoxalinone based inhibitors Rattus norvegicus
1.1.1.21 N-(tert-butyl)-3-(4-(4-nitrobenzyl)-3-oxo-3,4-dihydroquinoxalin-2-ylacryl amide
-
 Rattus norvegicus

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.2 Rattus norvegicus P51635
-
-
1.1.1.2 Rattus norvegicus Wistar P51635
-
-
1.1.1.21 Rattus norvegicus P07943
-
-
1.1.1.21 Rattus norvegicus Wistar P07943
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.2 additional information ALR1 is present in all tissues Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.2 D-glucuronate + NADPH + H+
-
 Rattus norvegicus ? + NADP+
-
 r
1.1.1.2 D-glucuronate + NADPH + H+
-
 Rattus norvegicus Wistar ? + NADP+
-
 r
1.1.1.21 D-glyceraldehyde + NADPH + H+
-
 Rattus norvegicus glycerol + NADP+
-
 r
1.1.1.21 D-glyceraldehyde + NADPH + H+
-
 Rattus norvegicus Wistar glycerol + NADP+
-
 r

Synonyms

EC Number Synonyms Comment Organism
1.1.1.2 alcohol dehydrogenase [NADP(+)] UniProt Rattus norvegicus
1.1.1.2 aldehyde reductase
-
 Rattus norvegicus
1.1.1.2 ALR1
-
 Rattus norvegicus
1.1.1.21 ALR2
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.2 37
-
 assay at, ALR1 Rattus norvegicus
1.1.1.21 30
-
 assay at, ALR2 Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.2 7.2
-
 assay at, ALR1 Rattus norvegicus
1.1.1.21 6.2
-
 assay at, ALR2 Rattus norvegicus

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.2 NADPH
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.2 0.000143
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(2-oxo-3-phenethylquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.000283
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(3-(2,4-difluorophenylamino)-6-nitro-2-oxoquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.000362
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(3-(4-fluorostyryl)-6-nitro-2-oxoquinoxalin-1(2H)-yl)acetic acid
1.1.1.2 0.00066
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(6-chloro-3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
1.1.1.2 0.00082
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.00114
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(3-(4-fluorophenethyl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.00143
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.00186
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(3-(3-(tert-butylamino)-3-oxoprop-1-en-1-yl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.00388
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(7-chloro-2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid
1.1.1.2 0.00753
-
 pH 7.2, 37°C, ALR1 Rattus norvegicus 2-(3-(4-(4-methoxyphenyl) piperazin-1-yl)-2-oxoquinoxalin-1(2H)-yl) acetic acid

General Information

EC Number General Information Comment Organism
1.1.1.2 physiological function ALR1 is present in all tissues and plays an important role in detoxification Rattus norvegicus
1.1.1.21 evolution aldose reductase (ALR2) is a member of aldo-keto reductase superfamily Rattus norvegicus