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Literature summary extracted from

  • Chiaradia, L.D.; Mascarello, A.; Purificacao, M.; Vernal, J.; Cordeiro, M.N.; Zenteno, M.E.; Villarino, A.; Nunes, R.J.; Yunes, R.A.; Terenzi, H.
    Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA (2008), Bioorg. Med. Chem. Lett., 18, 6227-6230.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.3.48 (2E)-1-(2'-hydroxyphenyl)-3-(1-naphthyl)-2-propen-1-one 76% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2,4-dimethoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 20% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2,4-dimethoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2,5-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one 58% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2,5-dimethoxyphenyl)-3-(naphth-1-yl)-2-propen-1-one 46% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one 8% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 16% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(2-hydroxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 26% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(3,4-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(3,4-dimethoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 68.5% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(3-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 20% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(3-methoxy-4-hydroxyphenyl)-3-(2-naphthyl)-2-propen-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(3-methoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 18.5% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(4-bromophenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 25% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(4-bromophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 11% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(4-hydroxy-3-methoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 39% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-1-(4-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 18% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one 8% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(2,5-dimethoxyphenyl)prop-2-en-1-one 9% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 18% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(3-nitrophenyl)prop-2-en-1-one 26% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one 14% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one 20% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one 6% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-(4-nitrophenyl)prop-2-en-1-one 19.5% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(1,3-benzodioxol-5-yl)-1-phenylprop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(3,4-dichlorophenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(3-chlorophenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 13% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(3-nitrophenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-1-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
-
 Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-1-yl)-1-(3-nitrophenyl)prop-2-en-1-one 12% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-1-yl)-1-(4-nitrophenyl)prop-2-en-1-one 18% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-1-yl)-1-phenylprop-2-en-1-one 37% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 9% activation at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-2-yl)-1-(3-nitrophenyl)prop-2-en-1-one 16% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-2-yl)-1-(4-nitrophenyl)prop-2-en-1-one 11% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 (2E)-3-(naphthalen-2-yl)-1-phenylprop-2-en-1-one 12% inhibition at 0.025 mM Mycobacterium tuberculosis
3.1.3.48 additional information synthesis and inhibitory activity of 38 synthetic chalcones towards PtpA, the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents, structure-activity analysis, overview. No inhibition by 3a, 3b, 3c, 4h, 5l, 6d, 6g, and 6j Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
3.1.3.48 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.3.48 4-nitrophenyl phosphate + H2O
-
 Mycobacterium tuberculosis 4-nitrophenol + phosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.1.3.48 protein tyrosine phosphatase
-
 Mycobacterium tuberculosis
3.1.3.48 PtpA
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.3.48 37
-
 assay at Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.3.48 8
-
 assay at Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.1.3.48 0.0084
-
 pH 8.0, 37°C Mycobacterium tuberculosis (2E)-1-(2,5-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one
3.1.3.48 0.0231
-
 pH 8.0, 37°C Mycobacterium tuberculosis (2E)-1-(3,4-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one
3.1.3.48 0.0395
-
 pH 8.0, 37°C Mycobacterium tuberculosis (2E)-1-(2,5-dimethoxyphenyl)-3-(naphth-1-yl)-2-propen-1-one
3.1.3.48 0.0502
-
 pH 8.0, 37°C Mycobacterium tuberculosis (2E)-1-(2'-hydroxyphenyl)-3-(1-naphthyl)-2-propen-1-one
3.1.3.48 0.0537
-
 pH 8.0, 37°C Mycobacterium tuberculosis (2E)-1-(3-methoxy-4-hydroxyphenyl)-3-(2-naphthyl)-2-propen-1-one