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Literature summary for 3.2.1.182 extracted from

  • Bharathkumar, H.; Sundaram, M.S.; Jagadish, S.; Paricharak, S.; Hemshekhar, M.; Mason, D.; Kemparaju, K.; Girish, K.S.; Basappa, K.S.; Bender, A.; Rangappa, K.S.
    Novel benzoxazine-based aglycones block glucose uptake in vivo by inhibiting glycosidases (2014), PLoS ONE, 9, e102759.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.2.1.182

Inhibitors

Inhibitors Comment Organism Structure
2-(1-(4-(2-cyanophenyl)benzyl-1H-indol-3-yl),2,4-dihydro-1H-benzo(d)(1,3))oxazine slight inhibition Rattus norvegicus
2-(1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
2-(2-butyl-4-chloro-1H-imidazol-5-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
2-(2-methyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
3-(2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)-4H-chromen-4-one slight inhibition Rattus norvegicus
3-(6-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)-4H-chromen-4-one
-
 Rattus norvegicus
3-(6-methyl-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)-4H-chromen-4-one slight inhibition Rattus norvegicus
4-(2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol
-
 Rattus norvegicus
4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol anti-hyperglycemic effect via glucose uptake inhibition by the inhibitor in the starved rat model Rattus norvegicus
6-chloro-2-(2-phenyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
6-methyl-2-(2-methyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
6-methyl-2-(2-phenyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
7-chloro-2-(1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
-
 Rattus norvegicus
acarbose
-
 Rattus norvegicus
additional information synthesis of a library of 1,3-benzoxazine scaffold based aglycones by using 2-aminobenzyl alcohols and aldehydes from one-pot reaction in a chloroacetic acid catalytic system via aerobic oxidative synthesis, inhibitory potencies of the compounds, molecular docking studies, overview Rattus norvegicus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O Rattus norvegicus
-
 (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?
(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O Rattus norvegicus Wistar
-
 (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?
(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O Rattus norvegicus
-
 (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?
(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O Rattus norvegicus Wistar
-
 (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-
Rattus norvegicus Wistar
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
intestine
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O
-
 Rattus norvegicus (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?
(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O
-
 Rattus norvegicus Wistar (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?
(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O
-
 Rattus norvegicus (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?
(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside + H2O
-
 Rattus norvegicus Wistar (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-ol + D-glucose
-
 ?

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Rattus norvegicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.9
-
 assay at Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0115
-
 pH 6.9, 37°C Rattus norvegicus 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol
0.0167
-
 pH 6.9, 37°C Rattus norvegicus 2-(2-butyl-4-chloro-1H-imidazol-5-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
0.0171
-
 pH 6.9, 37°C Rattus norvegicus 4-(2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol
0.0205
-
 pH 6.9, 37°C Rattus norvegicus 6-methyl-2-(2-phenyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
0.0216
-
 pH 6.9, 37°C Rattus norvegicus 2-(2-methyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
0.0238
-
 pH 6.9, 37°C Rattus norvegicus 6-methyl-2-(2-methyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
0.0277
-
 pH 6.9, 37°C Rattus norvegicus 7-chloro-2-(1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
0.0278
-
 pH 6.9, 37°C Rattus norvegicus 6-chloro-2-(2-phenyl-1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine
0.0319
-
 pH 6.9, 37°C Rattus norvegicus 3-(6-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)-4H-chromen-4-one
0.032
-
 pH 6.9, 37°C Rattus norvegicus 2-(1H-indol-3-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine