Any feedback?
Literature summary for 2.7.7.23 extracted from
- Exploring MDR-TB inhibitory potential of 4-aminoquinazolines as Mycobacterium tuberculosis N-acetylglucosamine-1-phosphate uridyltransferase (GlmUMTB) inhibitors (2020), Chem. Biodivers., 17, e2000237 .
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 2-2-[(6-nitroquinazolin-4-yl)amino]ethoxy)-ethan-1-ol | - |
Mycobacterium tuberculosis |  |
| 2-[2-[(6-nitroquinazolin-4-yl)amino]ethoxy]-ethan-1-ol | - |
Mycobacterium tuberculosis | |
| 4-(5-[(6-nitroquinazolin-4-yl)amino]-1,3,4-thiadiazol-2-yl)phenol | - |
Mycobacterium tuberculosis | |
| 4-(6-nitroquinazolin-4-ylamino)benzoic acid | - |
Mycobacterium tuberculosis | |
| 4-methyl-7-[(6-nitroquinazolin-4-yl)amino]-2H-1-benzopyran-2-one | - |
Mycobacterium tuberculosis | |
| 4-[(6-nitroquinazolin-4-yl)amino]-N-(pyrimidin-2-yl)benzene-1-sulfonamide | - |
Mycobacterium tuberculosis | |
| 4-[5-[(6-nitroquinazolin-4-yl)amino]-1,3,4-thiadiazol-2-yl]phenol | - |
Mycobacterium tuberculosis | |
| 6-nitro-N-(1,3-thiazol-2-yl)quinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 6-nitro-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 6-nitro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)quinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 6-nitro-N-(pyridin-2-ylmethyl)quinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 6-nitro-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 6-nitro-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]quinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 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 | |
| N-(1-benzylpiperidin-4-yl)-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| N-(2,4-dimethylphenyl)-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| N-(3-methylpiperazin-1-yl)-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| N-(4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl)acetamide | - |
Mycobacterium tuberculosis | |
| N-(5-methyl-1,3,4-thiadiazol-2-yl)-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| 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 | |
| N-cyclohexyl-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| N-cyclopropyl-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| N-[4-[(6,7-dimethoxyquinazolin-4-yl)amino]phenyl]-3-methoxybenzamide | 38% inhibition; 38% inhibition at 0.05 mM | Mycobacterium tuberculosis | |
| N-[4-[(6,7-dimethoxyquinazolin-4-yl)amino]phenyl]benzamide | 44% inhibition; 44% inhibition at 0.05 mM | Mycobacterium tuberculosis | |
| N-[4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl]acetamide | - |
Mycobacterium tuberculosis | |
| N-[4-[(7-hydroxy-6-methoxyquinazolin-4-yl)amino]phenyl]benzamide | 36% inhibition; 36% inhibition at 0.05 mM | Mycobacterium tuberculosis | |
| N-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-nitroquinazolin-4-amine | - |
Mycobacterium tuberculosis | |
| N1-(6-nitroquinazolin-4-yl)benzene-1,2-diamine | - |
Mycobacterium tuberculosis | |
| rifampicin | - |
Mycobacterium tuberculosis | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| UTP + N-acetyl-alpha-D-glucosamine 1-phosphate | Mycobacterium tuberculosis | - |
diphosphate + UDP-N-acetyl-alpha-D-glucosamine | - |
? | |
| UTP + N-acetyl-alpha-D-glucosamine 1-phosphate | Mycobacterium tuberculosis H37Rv | - |
diphosphate + UDP-N-acetyl-alpha-D-glucosamine | - |
? | |
| UTP + N-acetyl-alpha-D-glucosamine 1-phosphate | Mycobacterium tuberculosis ATCC 25618 | - |
diphosphate + UDP-N-acetyl-alpha-D-glucosamine | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Mycobacterium tuberculosis | P9WMN3 | - |
- |
| Mycobacterium tuberculosis ATCC 25618 | P9WMN3 | - |
- |
| Mycobacterium tuberculosis H37Rv | P9WMN3 | - |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| UTP + N-acetyl-alpha-D-glucosamine 1-phosphate | - |
Mycobacterium tuberculosis | diphosphate + UDP-N-acetyl-alpha-D-glucosamine | - |
? | |
| UTP + N-acetyl-alpha-D-glucosamine 1-phosphate | - |
Mycobacterium tuberculosis H37Rv | diphosphate + UDP-N-acetyl-alpha-D-glucosamine | - |
? | |
| UTP + N-acetyl-alpha-D-glucosamine 1-phosphate | - |
Mycobacterium tuberculosis ATCC 25618 | diphosphate + UDP-N-acetyl-alpha-D-glucosamine | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| GlmU | - |
Mycobacterium tuberculosis |
| GlmUMTB | - |
Mycobacterium tuberculosis |
| N-acetylglucosamine-1-phosphate uridyltransferase | - |
Mycobacterium tuberculosis |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.0000063 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | rifampicin | |
| 0.0029 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-(1-benzylpiperidin-4-yl)-6-nitroquinazolin-4-amine | |
| 0.0064 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-carbamimidoyl-4-[(6-nitroquinazolin-4-yl)-amino]benzene-1-sulfonamide | |
| 0.0087 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 2-2-[(6-nitroquinazolin-4-yl)amino]ethoxy)-ethan-1-ol | |
| 0.0087 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 2-[2-[(6-nitroquinazolin-4-yl)amino]ethoxy]-ethan-1-ol | |
| 0.0104 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N1-(6-nitroquinazolin-4-yl)benzene-1,2-diamine | |
| 0.016 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 6-nitro-N-(1,3-thiazol-2-yl)quinazolin-4-amine | |
| 0.021 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 6-nitro-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine | |
| 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 | |
| 0.023 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 6-nitro-N-(pyridin-2-ylmethyl)quinazolin-4-amine | |
| 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 | |
| 0.028 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-(4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl)acetamide | |
| 0.028 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-[4-[(6-nitroquinazolin-4-yl)amino]benzene-1-sulfonyl]acetamide | |
| 0.042 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 4-(6-nitroquinazolin-4-ylamino)benzoic acid | |
| 0.052 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-(2,4-dimethylphenyl)-6-nitroquinazolin-4-amine | |
| 0.121 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-cyclopropyl-6-nitroquinazolin-4-amine | |
| 0.141 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-cyclohexyl-6-nitroquinazolin-4-amine | |
| 0.194 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | N-(3-methylpiperazin-1-yl)-6-nitroquinazolin-4-amine | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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
| General Information | Comment | Organism |
|---|---|---|
| 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 |
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
Legal
Curated at
Member of
