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Literature summary for 6.3.2.1 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

Inhibitors Comment Organism Structure
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
5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxylic acid 0.1 mM, 12% inhibition 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 0.1 mM, 78% inhibition Mycobacterium tuberculosis
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
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
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
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
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
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
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
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
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
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
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
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
N-(2,5-dibromophenyl)-2-hydroxybenzamide
-
Mycobacterium tuberculosis
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
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
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
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

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

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WIL5
-
-
Mycobacterium tuberculosis 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 H37Rv AMP + diphosphate + (R)-pantothenate
-
?

Synonyms

Synonyms Comment Organism
Pantothenate synthetase
-
Mycobacterium tuberculosis

Cofactor

Cofactor Comment Organism Structure
ATP
-
Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
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
97
-
-
Mycobacterium tuberculosis N-(1-benzyl-1H-pyrazol-4-yl)-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
120
-
-
Mycobacterium tuberculosis 5-tert-butyl-N-[1-(2-methylbenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
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
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
140
-
-
Mycobacterium tuberculosis 5-tert-butyl-N-[1-(4-chlorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
140
-
-
Mycobacterium tuberculosis N-[1-(2-bromobenzyl)-1H-pyrazol-4-yl]-5-tert-butyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
150
-
-
Mycobacterium tuberculosis 5-tert-butyl-N-[1-(4-fluorobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
160
-
-
Mycobacterium tuberculosis 5-tert-butyl-N-[1-(2-iodobenzyl)-1H-pyrazol-4-yl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
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
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
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
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
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
61000
-
-
Mycobacterium tuberculosis 5-tert-butyl-N-1H-pyrazol-4-yl-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide