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Literature summary extracted from

  • Joshi, S.D.; More, U.A.; Dixit, S.R.; Balmi, S.V.; Kulkarni, B.G.; Ullagaddi, G.; Lherbet, C.; Aminabhavi, T.M.
    Chemical synthesis and in silico molecular modeling of novel pyrrolyl benzohydrazide derivatives Their biological evaluation against enoyl ACP reductase (InhA) and Mycobacterium tuberculosis (2017), Bioorg. Chem., 75, 181-200 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.3.1.9 expressed in Escherichia coli BL21 cells Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.1.9 1-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-1,2-diazepane-3,7-dione 18% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 1-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-1,2-dihydropyridazine-3,6-dione less than 5% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 1-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-4-methyl-1,2-dihydropyridazine-3,6-dione 42% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 1-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-4-methylenetetrahydropyridazine-3,6-dione 50% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 1-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)tetrahydropyridazine-3,6-dione 32% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 1-(4-(1H-pyrrol-1-yl)benzoyl)-1,2-diazepane-3,7-dione 27% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 1-(4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl)-1,2-diazepane-3,7-dione 13% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-2,3-dihydrophthalazine-1,4-dione 63% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-5,6,7,8-tetrabromo-2,3-dihydrophthalazine-1,4-dione 11% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-5,6,7,8-tetrachloro-2,3-dihydrophthalazine-1,4-dione 12% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)octahydrophthalazine-1,4-dione less than 5% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)benzoyl)-5,6,7,8-tetrabromo-2,3-dihydrophthalazine-1,4-dione 72% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)benzoyl)-5,6,7,8-tetrachloro-2,3-dihydrophthalazine-1,4-dione 64% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(1-(4-bromophenyl)ethylidene)acetohydrazide 27% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(1-(4-chlorophenyl)ethylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(1-(4-hydroxyphenyl)ethylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(1-(4-nitrophenyl)ethylidene)acetohydrazide 51% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(1-phenylethylidene)acetohydrazide 34% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(2,3-dichlorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(2,4-dichlorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(2,4-dimethoxybenzylidene)acetohydrazide 37% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(2,6-dichlorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(2-chlorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(2-nitrobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(3,4-dichlorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(3-bromobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(3-ethoxy-4-hydroxybenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(3-hydroxybenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(3-methoxybenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(3-phenoxybenzylidene)acetohydrazide 15% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-chlorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-fluorobenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-hydroxy-3-methoxybenzylideneacetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-hydroxybenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-isopropylbenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-methoxybenzylidene)acetohydrazide 21% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-(4-methylbenzylidene)acetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N'-benzylideneacetohydrazide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(1,3-dioxoisoindolin-2-yl)acetamide 25% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(1,3-dioxooctahydro-2H-isoindol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(2,5-dioxo-2,5-dihydro-1Hpyrrol-1-yl)acetamide 10% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(2,5-dioxopyrrolidin-1-yl)acetamide less than 5% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(2,6-dioxopiperidin-1-yl)acetamide 20% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetamide 10% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(3-methylene-2,5-dioxopyrrolidin-1-yl)acetamide 21% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(1H-pyrrol-1-yl)phenoxy)-N-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl)-5,6,7,8-tetrabromo-2,3-dihydrophthalazine-1,4-dione 75% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl)-5,6,7,8-tetrachloro-2,3-dihydrophthalazine-1,4-dione 76% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 5-((4-(1H-pyrrol-1-yl)phenoxy)methyl)-1,3,4-oxadiazole-2-thiol 57% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 5-((4-(1H-pyrrol-1-yl)phenoxy)methyl)-4-amino-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
 Mycobacterium tuberculosis
1.3.1.9 isoniazid
-
 Mycobacterium tuberculosis
1.3.1.9 N'-((1H-indol-3-yl)methylene)2-(4-(1H-pyrrol-1-yl)phenoxy)acetohydrazide 19% inhibition at 0.05 mM Mycobacterium tuberculosis
1.3.1.9 opiniazide
-
 Mycobacterium tuberculosis
1.3.1.9 phtivazid
-
 Mycobacterium tuberculosis
1.3.1.9 triclosan more than 99% inhibition at 0.05 mM Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.3.1.9 trans-DELTA2-enoyl-[acyl-carrier protein] + NADH + H+ Mycobacterium tuberculosis
-
 acyl-[acyl-carrier protein] + NAD+
-
 ?
1.3.1.9 trans-DELTA2-enoyl-[acyl-carrier protein] + NADH + H+ Mycobacterium tuberculosis H37Rv
-
 acyl-[acyl-carrier protein] + NAD+
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.9 Mycobacterium tuberculosis P9WGR1
-
-
1.3.1.9 Mycobacterium tuberculosis H37Rv P9WGR1
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.3.1.9 Ni-NTA agarose column chromatography Mycobacterium tuberculosis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.9 trans-2-dodecenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis dodecanoyl-CoA + NAD+
-
 ?
1.3.1.9 trans-2-dodecenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis H37Rv dodecanoyl-CoA + NAD+
-
 ?
1.3.1.9 trans-DELTA2-enoyl-[acyl-carrier protein] + NADH + H+
-
 Mycobacterium tuberculosis acyl-[acyl-carrier protein] + NAD+
-
 ?
1.3.1.9 trans-DELTA2-enoyl-[acyl-carrier protein] + NADH + H+
-
 Mycobacterium tuberculosis H37Rv acyl-[acyl-carrier protein] + NAD+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.1.9 2-trans-enoyl-ACP reductase
-
 Mycobacterium tuberculosis
1.3.1.9 InhA
-
 Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
1.3.1.9 NADH
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.3.1.9 0.0126
-
 at pH 6.8 and 25°C Mycobacterium tuberculosis 2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl)-5,6,7,8-tetrabromo-2,3-dihydrophthalazine-1,4-dione
1.3.1.9 0.0311
-
 at pH 6.8 and 25°C Mycobacterium tuberculosis 2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl)-5,6,7,8-tetrachloro-2,3-dihydrophthalazine-1,4-dione
1.3.1.9 0.05
-
 at pH 6.8 and 25°C Mycobacterium tuberculosis 1-(2-(4-(1H-pyrrol-1-yl)phenoxy)acetyl)-4-methylenetetrahydropyridazine-3,6-dione