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Literature summary for 6.3.2.1 extracted from

  • Samala, G.; Devi, P.B.; Saxena, S.; Meda, N.; Yogeeswari, P.; Sriram, D.
    Design, synthesis and biological evaluation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors (2016), Bioorg. Med. Chem., 24, 1298-1307 .
    View publication on PubMed
Search for more literature for 6.3.2.1

Cloned(Commentary)

Cloned (Comment) Organism
gene panC, recombinant expression in Escherichia coli strain BL21(DE3) Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
2-methyl-N'-(3,4,5-trimethoxybenzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
2-methyl-N'-(4-(trifluoromethyl)benzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
2-methyl-N'-(4-methylbenzoyl)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
2-methyl-N'-(4-phenoxybenzoyl)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
2-methyl-N-phenylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
6-methyl-N'-(3,4,5-trimethoxybenzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6-methyl-N'-(4-(trifluoromethyl)benzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6-methyl-N'-(4-methylbenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6-methyl-N'-(4-phenoxybenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6-methyl-N-phenylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
ethambutol
-
 Mycobacterium tuberculosis
isoniazid
-
 Mycobacterium tuberculosis
additional information design of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives from earlier reported imidazo[1,2-a]pyridine based Mycobacterium tuberculosis (MTB) pantothenate synthetase inhibitors, evaluation of thirty compounds as enzyme inhibitors and anti-tuberculosis agents, inhibition study of in vitro anti-TB activities against replicative and non-replicative MTB, in vivo activity using Mycobacterium marinum infected Zebra fish, and cytotoxicity against RAW 264.7 cell line, overview. No inhibition by amoxicillin Mycobacterium tuberculosis
moxifloxacin
-
 Mycobacterium tuberculosis
N'-(1-naphthoyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(1-naphthoyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(4-(dimethylamino)benzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(4-(dimethylamino)benzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(4-bromobenzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(4-bromobenzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(cyclohexanecarbonyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
N'-(cyclohexanecarbonyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
N'-benzoyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
N'-benzoyl-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
N'-benzylidene-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
N'-benzylidene-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
N-(4-bromophenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
N-(4-bromophenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
N-(4-ethoxyphenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
N-(4-methoxyphenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
N-benzyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
N-benzyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
N-cyclohexyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
N-cyclohexyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
rifampicin
-
 Mycobacterium tuberculosis

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + (R)-pantoate + beta-alanine Mycobacterium tuberculosis
-
 AMP + diphosphate + (R)-pantothenate
-
 ?
ATP + (R)-pantoate + beta-alanine Mycobacterium tuberculosis ATCC 27294 / ATCC 25618 / H37Rv
-
 AMP + diphosphate + (R)-pantothenate
-
 ?

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WIL5
-
-
Mycobacterium tuberculosis ATCC 27294 / ATCC 25618 / H37Rv P9WIL5
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + (R)-pantoate + beta-alanine
-
 Mycobacterium tuberculosis AMP + diphosphate + (R)-pantothenate
-
 ?
ATP + (R)-pantoate + beta-alanine
-
 Mycobacterium tuberculosis ATCC 27294 / ATCC 25618 / H37Rv AMP + diphosphate + (R)-pantothenate
-
 ?

Synonyms

Synonyms Comment Organism
PanC
-
 Mycobacterium tuberculosis
Pantothenate synthetase
-
 Mycobacterium tuberculosis
Rv3602c
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Mycobacterium tuberculosis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.8
-
 assay at Mycobacterium tuberculosis

Cofactor

Cofactor Comment Organism Structure
ATP
-
 Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00052
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-bromophenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
0.00053
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 2-methyl-N'-(4-phenoxybenzoyl)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.00058
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzylidene-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
0.00064
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(1-naphthoyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
0.00067
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(4-(trifluoromethyl)benzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
0.00069
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-bromophenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
0.00074
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N-phenylimidazo[2,1-b]thiazole-5-carboxamide
0.00084
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-benzyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
0.00102
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-bromobenzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.00102
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-cyclohexyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
0.00103
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 2-methyl-N-phenylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
0.00106
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-benzyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
0.0011
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzoyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.0012
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-bromobenzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
0.00123
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(4-phenoxybenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
0.00139
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(1-naphthoyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.00146
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-(dimethylamino)benzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.002
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-cyclohexyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
0.00207
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 2-methyl-N'-(3,4,5-trimethoxybenzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.0021
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-ethoxyphenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
0.00215
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzylidene-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.0025
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-(dimethylamino)benzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
0.00291
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(cyclohexanecarbonyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.00499
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(4-methylbenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
0.00531
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 2-methyl-N'-(4-(trifluoromethyl)benzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.00531
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzoyl-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
0.00538
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(cyclohexanecarbonyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
0.00561
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(3,4,5-trimethoxybenzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
0.00583
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 2-methyl-N'-(4-methylbenzoyl)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
0.00583
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-methoxyphenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
0.025
-
 above, pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis isoniazid
0.025
-
 above, pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis ethambutol