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Literature summary for 1.3.1.118 extracted from

  • Pedgaonkar, G.; Sridevi, J.; Jeankumar, V.; Saxena, S.; Devi, P.; Renuka, J.; Yogeeswari, P.; Sriram, D.
    Development of 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis (2014), Eur. J. Med. Chem., 86, 613-627 .
    View publication on PubMed
Search for more literature for 1.3.1.118

Application

Application Comment Organism
pharmacology the enzyme is a target for developing novel anti-tubercular agents Mycobacterium tuberculosis

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli BL21 (DE3) Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
2-(4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
2-(4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
additional information twenty eight 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives are synthesized and evaluated for their in vitro Mycobacterium tuberculosis InhA inhibition. Compounds are evaluated for their in vitro activity against drug sensitive and resistant Mycobacterium tuberculosis strains and cytotoxicity against RAW 264.7 cell line. Compounds are docked at the active site of InhA to understand their binding mode and differential scanning fluorimetry is performed to ascertain their protein interaction and stability Mycobacterium tuberculosis
N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(5-nitrothiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(benzo[d]thiazol-2-yl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(benzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(furan-2-yl-methyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WGR1
-
-
Mycobacterium tuberculosis ATCC 25618 P9WGR1
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
trans-2-decenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis decanoyl-CoA + NAD+
-
 ?
trans-2-decenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis ATCC 25618 decanoyl-CoA + NAD+
-
 ?

Synonyms

Synonyms Comment Organism
enoyl acyl carrier protein reductase
-
 Mycobacterium tuberculosis
InhA
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Mycobacterium tuberculosis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.8
-
 assay at Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00312
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
0.00312
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
0.00452
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
0.00456
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
0.00512
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
0.00601
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
0.00616
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
0.00676
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
0.00686
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
0.00712
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
0.00716
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
0.00778
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
0.00816
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
0.00836
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
0.00892
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
0.00906
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide