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Literature summary extracted from

  • Velaparthi, S.; Brunsteiner, M.; Uddin, R.; Wan, B.; Franzblau, S.G.; Petukhov, P.A.
    5-tert-butyl-N-pyrazol-4-yl-4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxamide derivatives as novel potent inhibitors of Mycobacterium tuberculosis pantothenate synthetase: initiating a quest for new antitubercular drugs (2008), J. Med. Chem., 51, 1999-2002.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.3.2.1 4-[(4-[[(5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)carbonyl]amino]-1H-pyrazol-1-yl)methyl]benzoic acid 0.1 mM, 99% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxylic acid 0.1 mM, 12% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-(1-[4-[(2-phenylethyl)carbamoyl]benzyl]-1H-pyrazol-4-yl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 78% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-1H-pyrazol-4-yl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 43% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-pyrazol-4-yl-4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxamide derivatives silico molecular design, synthesis, and inhibitory activity, overview Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(2,4,6-trichlorophenyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 17% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(2,4-difluorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 100% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(2-iodobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 84% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(2-methylbenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 89% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(4-chlorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 98% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(4-fluorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 98% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[1-(naphthalen-2-ylmethyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 97% inhibition Mycobacterium tuberculosis
6.3.2.1 5-tert-butyl-N-[4-carbamoyl-3-(4-methoxybenzyl)isoxazol-5-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 79% inhibition Mycobacterium tuberculosis
6.3.2.1 methyl 4-[(4-[[(5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)carbonyl]amino]-1H-pyrazol-1-yl)methyl]benzoate 0.1 mM, 100% inhibition Mycobacterium tuberculosis
6.3.2.1 N-(1-benzyl-1H-pyrazol-4-yl)-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 100% inhibition Mycobacterium tuberculosis
6.3.2.1 N-(2,5-dibromophenyl)-2-hydroxybenzamide
-
 Mycobacterium tuberculosis
6.3.2.1 N-[1-(2,4-dichlorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 18% inhibition Mycobacterium tuberculosis
6.3.2.1 N-[1-(2-bromobenzyl)-1H-pyrazol-4-yl]-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 94% inhibition Mycobacterium tuberculosis
6.3.2.1 N-[1-[4-(benzylcarbamoyl)benzyl]-1H-pyrazol-4-yl]-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide 0.1 mM, 82% inhibition Mycobacterium tuberculosis
6.3.2.1 tert-butyl 4-[(4-[[(5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)carbonyl]amino]-1H-pyrazol-1-yl)methyl]benzoate 0.1 mM, 79% inhibition Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
6.3.2.1 Mg2+
-
 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 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 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 H37Rv AMP + diphosphate + (R)-pantothenate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
6.3.2.1 Pantothenate synthetase
-
 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 90
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[1-(naphthalen-2-ylmethyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 97
-
-
 Mycobacterium tuberculosis N-(1-benzyl-1H-pyrazol-4-yl)-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 120
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[1-(2-methylbenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 130
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[1-(2,4-difluorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 140
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-(1-[4-[(2-phenylethyl)carbamoyl]benzyl]-1H-pyrazol-4-yl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 140
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[1-(4-chlorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 140
-
-
 Mycobacterium tuberculosis N-[1-(2-bromobenzyl)-1H-pyrazol-4-yl]-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 150
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[1-(4-fluorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 160
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[1-(2-iodobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 160
-
-
 Mycobacterium tuberculosis methyl 4-[(4-[[(5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)carbonyl]amino]-1H-pyrazol-1-yl)methyl]benzoate
6.3.2.1 210
-
-
 Mycobacterium tuberculosis N-[1-[4-(benzylcarbamoyl)benzyl]-1H-pyrazol-4-yl]-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 250
-
-
 Mycobacterium tuberculosis tert-butyl 4-[(4-[[(5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)carbonyl]amino]-1H-pyrazol-1-yl)methyl]benzoate
6.3.2.1 460
-
-
 Mycobacterium tuberculosis 4-[(4-[[(5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)carbonyl]amino]-1H-pyrazol-1-yl)methyl]benzoic acid
6.3.2.1 7130
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-[4-carbamoyl-3-(4-methoxybenzyl)isoxazol-5-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
6.3.2.1 61000
-
-
 Mycobacterium tuberculosis 5-tert-butyl-N-1H-pyrazol-4-yl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide