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Literature summary for 3.4.21.1 extracted from

  • Marasini, B.P.; Rahim, F.; Perveen, S.; Karim, A.; Mohammed Khan, K.; Atta-Ur-Rahman, K.; Choudhary, M.I.
    Synthesis, structure-activity relationships studies of benzoxazinone derivatives as alpha-chymotrypsin inhibitors (2017), Bioorg. Chem., 70, 210-221 .
    View publication on PubMed
Search for more literature for 3.4.21.1

Inhibitors

Inhibitors Comment Organism Structure
2-(2,6-difluorophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(2,6-dimethoxyphenyl)-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
2-(2-bromophenyl)-4H-3,1-benzoxazin-4-one competitive inhibition Bos taurus
2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
2-(2-methoxyphenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one competitive inhibition Bos taurus
2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(2-thienyl)-4H-3,1-benzoxazin-4-one competitive inhibition Bos taurus
2-(3,4,5-trimethoxyphenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(3-bromophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(3-bromophenyl)-7-nitro-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(3-chlorophenyl)-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
2-(3-chlorophenyl)-7-methyl-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(3-fluorophenyl)-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
2-(3-methylphenyl)-4H-3,1-benzoxazin-4-one competitive inhibition Bos taurus
2-(3-methylphenyl)-7-nitro-4H-3,1-benzoxazin-4-one competitive inhibition Bos taurus
2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(4-bromophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(4-fluorophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(4-methoxyphenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-(4-methylphenyl)-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
2-(4-nitrophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
2-phenyl-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
4-methyl-N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]benzenesulfonamide non-competitive inhibition Bos taurus
7-chloro-2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one mixed-type inhibition Bos taurus
7-chloro-2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
7-chloro-2-(4-nitrophenyl)-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
7-chloro-2-phenyl-4H-3,1-benzoxazin-4-one non-competitive inhibition Bos taurus
benzoxazinone the presence of substituents on benzene ring reduces the inhibitory potential of benzoxazinone. The increased inhibitory potential due to fluoro group at phenyl substituent is observed followed by chloro and bromo substituents. Compounds with strong electron donating or withdrawing groups on phenyl substituent, show a good inhibitory potential at ortho > meta > para position. Kinetic studies show diverse types of inhibition, except uncompetitive-type inhibition Bos taurus
chymostatin competitive inhibition Bos taurus

Organism

Organism UniProt Comment Textmining
Bos taurus P00766
-
-

Source Tissue

Source Tissue Comment Organism Textmining
pancreas
-
 Bos taurus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
N-succinyl-L-phenylalanine-p-nitroanilide + H2O
-
 Bos taurus N-succinyl-L-phenylalanine + p-nitroaniline
-
 ?

Synonyms

Synonyms Comment Organism
alpha-chymotrypsin
-
 Bos taurus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00047
-
 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0026
-
 chymostatin pH 7.6, 30°C Bos taurus
0.0087
-
 2-phenyl-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0091
-
 2-(2-thienyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0091
-
 2-(2-bromophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0098
-
 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0125
-
 2-(2-methoxyphenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0126
-
 2-(4-methoxyphenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0161
-
 2-(3-methylphenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.01619
-
 2-(3-methylphenyl)-7-nitro-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0164
-
 2-(4-methylphenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0178
-
 2-(3-fluorophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0224
-
 2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0226
-
 2-(3-chlorophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0277
-
 2-(2,6-dimethoxyphenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.0301
-
 2-(2,6-difluorophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.094
-
 2-(4-fluorophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.303
-
 7-chloro-2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus
0.341
-
 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one pH 7.6, 30°C Bos taurus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0058
-
 pH 7.6, 30°C Bos taurus chymostatin
0.0065
-
 pH 7.6, 30°C Bos taurus 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one
0.0099
-
 pH 7.6, 30°C Bos taurus 2-(2-methoxyphenyl)-4H-3,1-benzoxazin-4-one
0.0117
-
 pH 7.6, 30°C Bos taurus 2-phenyl-4H-3,1-benzoxazin-4-one
0.0121
-
 pH 7.6, 30°C Bos taurus 2-(2-thienyl)-4H-3,1-benzoxazin-4-one
0.0144
-
 pH 7.6, 30°C Bos taurus 2-(4-methoxyphenyl)-4H-3,1-benzoxazin-4-one
0.0188
-
 pH 7.6, 30°C Bos taurus 2-(2-bromophenyl)-4H-3,1-benzoxazin-4-one
0.0201
-
 pH 7.6, 30°C Bos taurus 2-(4-methylphenyl)-4H-3,1-benzoxazin-4-one
0.0235
-
 pH 7.6, 30°C Bos taurus 2-(2,6-difluorophenyl)-4H-3,1-benzoxazin-4-one
0.0238
-
 pH 7.6, 30°C Bos taurus 2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one
0.0239
-
 pH 7.6, 30°C Bos taurus 2-(3-methylphenyl)-4H-3,1-benzoxazin-4-one
0.0263
-
 pH 7.6, 30°C Bos taurus 2-(2,6-dimethoxyphenyl)-4H-3,1-benzoxazin-4-one
0.0282
-
 pH 7.6, 30°C Bos taurus 2-(3-fluorophenyl)-4H-3,1-benzoxazin-4-one
0.0288
-
 pH 7.6, 30°C Bos taurus 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one
0.0418
-
 pH 7.6, 30°C Bos taurus 2-(3-chlorophenyl)-4H-3,1-benzoxazin-4-one
0.0941
-
 pH 7.6, 30°C Bos taurus 2-(3-methylphenyl)-7-nitro-4H-3,1-benzoxazin-4-one
0.159
-
 pH 7.6, 30°C Bos taurus 2-(4-fluorophenyl)-4H-3,1-benzoxazin-4-one
0.314
-
 pH 7.6, 30°C Bos taurus 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one
0.329
-
 pH 7.6, 30°C Bos taurus 7-chloro-2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one