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Literature summary extracted from

  • Patel, H.M.; Palkar, M.; Karpoormath, R.
    Exploring MDR-TB inhibitory potential of 4-aminoquinazolines as Mycobacterium tuberculosis N-acetylglucosamine-1-phosphate uridyltransferase (GlmUMTB) inhibitors (2020), Chem. Biodivers., 17, e2000237 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.7.7.23 2-2-[(6-nitroquinazolin-4-yl)amino]ethoxy)-ethan-1-ol
-
 Mycobacterium tuberculosis
2.7.7.23 2-[2-[(6-nitroquinazolin-4-yl)amino]ethoxy]-ethan-1-ol
-
 Mycobacterium tuberculosis
2.7.7.23 4-(5-[(6-nitroquinazolin-4-yl)amino]-1,3,4-thiadiazol-2-yl)phenol
-
 Mycobacterium tuberculosis
2.7.7.23 4-(6-nitroquinazolin-4-ylamino)benzoic acid
-
 Mycobacterium tuberculosis
2.7.7.23 4-methyl-7-[(6-nitroquinazolin-4-yl)amino]-2H-1-benzopyran-2-one
-
 Mycobacterium tuberculosis
2.7.7.23 4-[(6-nitroquinazolin-4-yl)amino]-N-(pyrimidin-2-yl)benzene-1-sulfonamide
-
 Mycobacterium tuberculosis
2.7.7.23 4-[5-[(6-nitroquinazolin-4-yl)amino]-1,3,4-thiadiazol-2-yl]phenol
-
 Mycobacterium tuberculosis
2.7.7.23 6-nitro-N-(1,3-thiazol-2-yl)quinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 6-nitro-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 6-nitro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)quinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 6-nitro-N-(pyridin-2-ylmethyl)quinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 6-nitro-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 6-nitro-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 additional information inhibitory potential of 4-aminoquinazolines as Mycobacterium tuberculosis N-acetylglucosamine-1-phosphate uridyltransferase (GlmUMTB) inhibitors, overview. Molecular docking using the crystal structure of GlmUMTB (PDB ID 3ST8), with bound substrates, N-acetylglucosamine-1-phosphate (NAcGlc-1-P) and uridine diphosphate-N-cetylglucosamine (UDP-GlcNAc). Analysis of inhibition of Mycobacterium tuberculosis wild-type strain H37Rv and of multiresistant strain MDR-MTB, antimycobacterial activity, MIC values for both strains; not inhibited by isoniazid Mycobacterium tuberculosis
2.7.7.23 N-(1-benzylpiperidin-4-yl)-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N-(2,4-dimethylphenyl)-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N-(3-methylpiperazin-1-yl)-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N-(4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl)acetamide
-
 Mycobacterium tuberculosis
2.7.7.23 N-(5-methyl-1,3,4-thiadiazol-2-yl)-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N-carbamimidoyl-4-[(6-nitroquinazolin-4-yl)-amino]benzene-1-sulfonamide compound with sulfaguanidine moiety at 4th position of quinazoline forms polar hydrogen bond with Glu 166 and Gln 205 via guanidine moiety. Lys 26 forms pi-pi stacking with the phenyl ring of sulfaguanidine and hydrogen bonding with the nitro functional g Mycobacterium tuberculosis
2.7.7.23 N-cyclohexyl-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N-cyclopropyl-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N-[4-[(6,7-dimethoxyquinazolin-4-yl)amino]phenyl]-3-methoxybenzamide 38% inhibition; 38% inhibition at 0.05 mM Mycobacterium tuberculosis
2.7.7.23 N-[4-[(6,7-dimethoxyquinazolin-4-yl)amino]phenyl]benzamide 44% inhibition; 44% inhibition at 0.05 mM Mycobacterium tuberculosis
2.7.7.23 N-[4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl]acetamide
-
 Mycobacterium tuberculosis
2.7.7.23 N-[4-[(7-hydroxy-6-methoxyquinazolin-4-yl)amino]phenyl]benzamide 36% inhibition; 36% inhibition at 0.05 mM Mycobacterium tuberculosis
2.7.7.23 N-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-nitroquinazolin-4-amine
-
 Mycobacterium tuberculosis
2.7.7.23 N1-(6-nitroquinazolin-4-yl)benzene-1,2-diamine
-
 Mycobacterium tuberculosis
2.7.7.23 rifampicin
-
 Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.7.7.23 UTP + N-acetyl-alpha-D-glucosamine 1-phosphate Mycobacterium tuberculosis
-
 diphosphate + UDP-N-acetyl-alpha-D-glucosamine
-
 ?
2.7.7.23 UTP + N-acetyl-alpha-D-glucosamine 1-phosphate Mycobacterium tuberculosis H37Rv
-
 diphosphate + UDP-N-acetyl-alpha-D-glucosamine
-
 ?
2.7.7.23 UTP + N-acetyl-alpha-D-glucosamine 1-phosphate Mycobacterium tuberculosis ATCC 25618
-
 diphosphate + UDP-N-acetyl-alpha-D-glucosamine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.7.7.23 Mycobacterium tuberculosis P9WMN3
-
-
2.7.7.23 Mycobacterium tuberculosis ATCC 25618 P9WMN3
-
-
2.7.7.23 Mycobacterium tuberculosis H37Rv P9WMN3
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.7.7.23 UTP + N-acetyl-alpha-D-glucosamine 1-phosphate
-
 Mycobacterium tuberculosis diphosphate + UDP-N-acetyl-alpha-D-glucosamine
-
 ?
2.7.7.23 UTP + N-acetyl-alpha-D-glucosamine 1-phosphate
-
 Mycobacterium tuberculosis H37Rv diphosphate + UDP-N-acetyl-alpha-D-glucosamine
-
 ?
2.7.7.23 UTP + N-acetyl-alpha-D-glucosamine 1-phosphate
-
 Mycobacterium tuberculosis ATCC 25618 diphosphate + UDP-N-acetyl-alpha-D-glucosamine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.7.7.23 GlmU
-
 Mycobacterium tuberculosis
2.7.7.23 GlmUMTB
-
 Mycobacterium tuberculosis
2.7.7.23 N-acetylglucosamine-1-phosphate uridyltransferase
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.7.7.23 0.0000063
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis rifampicin
2.7.7.23 0.0029
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-(1-benzylpiperidin-4-yl)-6-nitroquinazolin-4-amine
2.7.7.23 0.0064
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-carbamimidoyl-4-[(6-nitroquinazolin-4-yl)-amino]benzene-1-sulfonamide
2.7.7.23 0.0087
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 2-2-[(6-nitroquinazolin-4-yl)amino]ethoxy)-ethan-1-ol
2.7.7.23 0.0087
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 2-[2-[(6-nitroquinazolin-4-yl)amino]ethoxy]-ethan-1-ol
2.7.7.23 0.0104
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N1-(6-nitroquinazolin-4-yl)benzene-1,2-diamine
2.7.7.23 0.016
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-(1,3-thiazol-2-yl)quinazolin-4-amine
2.7.7.23 0.021
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine
2.7.7.23 0.021
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine
2.7.7.23 0.023
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-(pyridin-2-ylmethyl)quinazolin-4-amine
2.7.7.23 0.026
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 4-[(6-nitroquinazolin-4-yl)amino]-N-(pyrimidin-2-yl)benzene-1-sulfonamide
2.7.7.23 0.028
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-(4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl)acetamide
2.7.7.23 0.028
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-[4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl]acetamide
2.7.7.23 0.042
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 4-(6-nitroquinazolin-4-ylamino)benzoic acid
2.7.7.23 0.052
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-(2,4-dimethylphenyl)-6-nitroquinazolin-4-amine
2.7.7.23 0.121
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-cyclopropyl-6-nitroquinazolin-4-amine
2.7.7.23 0.141
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-cyclohexyl-6-nitroquinazolin-4-amine
2.7.7.23 0.194
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis N-(3-methylpiperazin-1-yl)-6-nitroquinazolin-4-amine
2.7.7.23 0.2
-
 above, pH and temperature not specified in the publication Mycobacterium tuberculosis 4-(5-[(6-nitroquinazolin-4-yl)amino]-1,3,4-thiadiazol-2-yl)phenol
2.7.7.23 0.2
-
 above, pH and temperature not specified in the publication Mycobacterium tuberculosis 4-methyl-7-[(6-nitroquinazolin-4-yl)amino]-2H-1-benzopyran-2-one
2.7.7.23 0.2
-
 above, pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)quinazolin-4-amine
2.7.7.23 0.2
-
 above, pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine
2.7.7.23 0.2
-
 above, pH and temperature not specified in the publication Mycobacterium tuberculosis N-(5-methyl-1,3,4-thiadiazol-2-yl)-6-nitroquinazolin-4-amine
2.7.7.23 0.2
-
 above, pH and temperature not specified in the publication Mycobacterium tuberculosis N-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-nitroquinazolin-4-amine
2.7.7.23 0.2
-
 IC50 above 0.2 mM, pH and temperature not specified in the publication Mycobacterium tuberculosis 4-methyl-7-[(6-nitroquinazolin-4-yl)amino]-2H-1-benzopyran-2-one
2.7.7.23 0.2
-
 IC50 above 0.2 mM, pH and temperature not specified in the publication Mycobacterium tuberculosis 4-[5-[(6-nitroquinazolin-4-yl)amino]-1,3,4-thiadiazol-2-yl]phenol
2.7.7.23 0.2
-
 IC50 above 0.2 mM, pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)quinazolin-4-amine
2.7.7.23 0.2
-
 IC50 above 0.2 mM, pH and temperature not specified in the publication Mycobacterium tuberculosis 6-nitro-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine
2.7.7.23 0.2
-
 IC50 above 0.2 mM, pH and temperature not specified in the publication Mycobacterium tuberculosis N-(5-methyl-1,3,4-thiadiazol-2-yl)-6-nitroquinazolin-4-amine
2.7.7.23 0.2
-
 IC50 above 0.2 mM, pH and temperature not specified in the publication Mycobacterium tuberculosis N-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-nitroquinazolin-4-amine

General Information

EC Number General Information Comment Organism
2.7.7.23 physiological function the bifunctional enzyme is found exclusively in bacteria and catalyzes the development of uridine diphosphate-N-acetylglucosamine (UDP-GlcNAc), an essential intermediate in peptidoglycan biosynthesis in Mycobacterium tuberculosis (Mtb) Mycobacterium tuberculosis