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Literature summary 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

Cloned(Commentary)

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.3.2.1 2-methyl-N'-(3,4,5-trimethoxybenzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 2-methyl-N'-(4-(trifluoromethyl)benzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 2-methyl-N'-(4-methylbenzoyl)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 2-methyl-N'-(4-phenoxybenzoyl)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 2-methyl-N-phenylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 6-methyl-N'-(3,4,5-trimethoxybenzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 6-methyl-N'-(4-(trifluoromethyl)benzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 6-methyl-N'-(4-methylbenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 6-methyl-N'-(4-phenoxybenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 6-methyl-N-phenylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 ethambutol
-
 Mycobacterium tuberculosis
6.3.2.1 isoniazid
-
 Mycobacterium tuberculosis
6.3.2.1 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
6.3.2.1 moxifloxacin
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(1-naphthoyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(1-naphthoyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(4-(dimethylamino)benzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(4-(dimethylamino)benzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(4-bromobenzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(4-bromobenzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(cyclohexanecarbonyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-(cyclohexanecarbonyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-benzoyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-benzoyl-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-benzylidene-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N'-benzylidene-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N-(4-bromophenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-(4-bromophenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-(4-ethoxyphenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-(4-methoxyphenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-benzyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-benzyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-cyclohexyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-cyclohexyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
-
 Mycobacterium tuberculosis
6.3.2.1 rifampicin
-
 Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
6.3.2.1 Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

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

Organism

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

Substrates and Products (Substrate)

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

Synonyms

EC Number Synonyms Comment Organism
6.3.2.1 PanC
-
 Mycobacterium tuberculosis
6.3.2.1 Pantothenate synthetase
-
 Mycobacterium tuberculosis
6.3.2.1 Rv3602c
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
6.3.2.1 37
-
 assay at Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
6.3.2.1 7.8
-
 assay at Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
6.3.2.1 ATP
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
6.3.2.1 0.00052
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-bromophenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
6.3.2.1 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
6.3.2.1 0.00058
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzylidene-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00064
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(1-naphthoyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00067
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(4-(trifluoromethyl)benzylidene)imidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00069
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-bromophenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
6.3.2.1 0.00074
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N-phenylimidazo[2,1-b]thiazole-5-carboxamide
6.3.2.1 0.00084
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-benzyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
6.3.2.1 0.00102
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-bromobenzylidene)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
6.3.2.1 0.00102
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-cyclohexyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
6.3.2.1 0.00103
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 2-methyl-N-phenylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
6.3.2.1 0.00106
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-benzyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
6.3.2.1 0.0011
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzoyl-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
6.3.2.1 0.0012
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-bromobenzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00123
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(4-phenoxybenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00139
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(1-naphthoyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
6.3.2.1 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
6.3.2.1 0.002
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-cyclohexyl-6-methylimidazo[2,1-b]thiazole-5-carboxamide
6.3.2.1 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
6.3.2.1 0.0021
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-ethoxyphenyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxamide
6.3.2.1 0.00215
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzylidene-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
6.3.2.1 0.0025
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(4-(dimethylamino)benzylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00291
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(cyclohexanecarbonyl)-2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide
6.3.2.1 0.00499
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis 6-methyl-N'-(4-methylbenzoyl)imidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 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
6.3.2.1 0.00531
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-benzoyl-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 0.00538
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N'-(cyclohexanecarbonyl)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
6.3.2.1 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
6.3.2.1 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
6.3.2.1 0.00583
-
 pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis N-(4-methoxyphenyl)-6-methylimidazo[2,1-b]thiazole-5-carboxamide
6.3.2.1 0.025
-
 above, pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis isoniazid
6.3.2.1 0.025
-
 above, pH 7.8, 37°C, recombinant enzyme Mycobacterium tuberculosis ethambutol