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Literature summary for 3.6.1.9 extracted from

  • Kuhrt, D.; Ejaz, S.A.; Afzal, S.; Khan, S.U.; Lecka, J.; Sevigny, J.; Ehlers, P.; Spannenberg, A.; Iqbal, J.; Langer, P.
    Chemoselective synthesis and biological evaluation of arylated 2-(Trifluoromethyl) quinolines as nucleotide pyrophosphatase (NPPs) inhibitors (2017), Eur. J. Med. Chem., 138, 816-829 .
    View publication on PubMed
Search for more literature for 3.6.1.9

Cloned(Commentary)

Cloned (Comment) Organism
gene ENPP1, recombinant expression in COS-7 cells Homo sapiens
gene ENPP3, recombinant expression in COS-7 cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
1,1'-(2-(2-bromophenyl)ethene-1,1-diyl)bis(1H-indole)
-
 Homo sapiens
2-(trifluoromethyl)-3,4,8-tri(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
3,4,8-tri(4-fluorophenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tri([1,1'-biphenyl]-4-yl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tri-(3-chlorophenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tri-m-tolyl-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tri-p-tolyl-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tribromo-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-triphenyl-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tris(3,5-dimethylphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,4,8-tris(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,8-dibromo-2-(trifluoromethyl)quinolin-4(1H)-one
-
 Homo sapiens
3,8-dibromo-4-(piperidin-1-yl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,8-dibromo-4-(pyrrolidin-1-yl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,8-dibromo-4-chloro-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3,8-dibromo-4-N-butylamine-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-(3-bromo-4-chloro-2-(trifluoromethyl)quinolin-8-yl)benzonitrile
-
 Homo sapiens
3-bromo-4-chloro-2-(trifluoromethyl)-8-(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-(2,5-dimethoxyphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-(3,5-difluorophenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-(3,5-dimethylphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-(o-tolyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-(thiophen-3-yl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-chloro-8-phenyl-2-(trifluoromethyl)quinoline
-
 Homo sapiens
3-bromo-4-N-butylamine-8-(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
4-(3,8-dibromo-2-(trifluoromethyl)quinolin-4-yl)morpholine
-
 Homo sapiens
4-chloro-2-(trifluoromethyl)-3,8-bis(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
4-chloro-3,8-bis(3-methylphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
4-chloro-3,8-bis(4-(trifluoromethoxy)phenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
4-chloro-3,8-bis(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
4-chloro-3,8-diphenyl-2-(trifluoromethyl)quinoline
-
 Homo sapiens
4-chloro-8-(2,5-dimethoxyphenyl)-2-(trifluoromethyl)-3-(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
4-chloro-8-phenyl-2-(trifluoromethyl)-3-(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
4-N-butylamine-3,8-bis(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
-
 Homo sapiens
8-(4-methoxyphenyl)-3,4-di-p-tolyl-2-(trifluoromethyl)quinoline
-
 Homo sapiens
8-phenyl-2-(trifluoromethyl)-3,4-bis(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
8-phenyl-4-(p-tolyl)-2-(trifluoromethyl)-3-(4-(trifluoromethyl)phenyl)quinoline
-
 Homo sapiens
additional information design and synthesis of arylated 2-trifluoromethylquinolines derivatives by site-selective, chemo-selective amination reactions following regioselective Suzuki-Miyaura coupling reactions. Evaluation of their potential to inhibit two families of ecto-nucleotidases, i.e. NPPs (EC 3.6.1.9) and nucleoside triphosphate diphosphohydrolases (NTPDases, EC 3.6.1.15), docking studies to analyze the active binding site of the molecules, overview. The compounds all show negligible inhibition of NTPDases1-3; design and synthesis of arylated 2-trifluoromethylquinolines derivatives by site-selective, chemo-selective amination reactions following regioselective Suzuki-Miyaura coupling reactions. Evaluation of their potential to inhibit two families of ecto-nucleotidases, i.e. NPPs (EC 3.6.1.9) and nucleoside triphosphate diphosphohydrolases (NTPDases, EC 3.6.1.15), docking studies to analyze the active binding site of the molecules, overview. The compounds all show negligible inhibition of NTPDases1-3 Homo sapiens

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Homo sapiens
Zn2+ required Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens O14638
-
-
Homo sapiens P22413
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl-5'-thymidine monophosphate + H2O
-
 Homo sapiens 4-nitrophenol + 5'-thymidine monophosphate
-
 ?

Synonyms

Synonyms Comment Organism
h-NPP1
-
 Homo sapiens
h-NPP3
-
 Homo sapiens
NPP1
-
 Homo sapiens
NPP3
-
 Homo sapiens
nucleotide pyrophosphatase
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
9.5
-
 assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00018
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3,4,8-triphenyl-2-(trifluoromethyl)quinoline
0.00025
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3-bromo-4-chloro-8-(2,5-dimethoxyphenyl)-2-(trifluoromethyl)quinoline
0.00031
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3-bromo-4-chloro-2-(trifluoromethyl)-8-(4-(trifluoromethyl)phenyl)quinoline
0.00035
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3-(3-bromo-4-chloro-2-(trifluoromethyl)quinolin-8-yl)benzonitrile
0.00036
-
 pH 9.5, 37°C, NPP3 Homo sapiens 3-bromo-4-chloro-8-(2,5-dimethoxyphenyl)-2-(trifluoromethyl)quinoline
0.00039
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3-bromo-4-chloro-8-(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
0.00039
-
 pH 9.5, 37°C, NPP3 Homo sapiens 3,8-dibromo-4-chloro-2-(trifluoromethyl)quinoline
0.00051
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3,4,8-tri(4-fluorophenyl)-2-(trifluoromethyl)quinoline
0.00073
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3,4,8-tri-p-tolyl-2-(trifluoromethyl)quinoline
0.00114
-
 pH 9.5, 37°C, NPP3 Homo sapiens 3-bromo-4-chloro-8-(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
0.00242
-
 pH 9.5, 37°C, NPP3 Homo sapiens 3,8-dibromo-2-(trifluoromethyl)quinolin-4(1H)-one
0.00281
-
 pH 9.5, 37°C, NPP1 Homo sapiens 4-chloro-3,8-diphenyl-2-(trifluoromethyl)quinoline
0.00576
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3-bromo-4-chloro-8-(thiophen-3-yl)-2-(trifluoromethyl)quinoline
0.00765
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3,8-dibromo-4-chloro-2-(trifluoromethyl)quinoline
0.00987
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3,4,8-tris(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
0.0207
-
 pH 9.5, 37°C, NPP1 Homo sapiens 3,4,8-tri-m-tolyl-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3,4,8-tri(4-fluorophenyl)-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3,4,8-tri-m-tolyl-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3,4,8-tri-p-tolyl-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3,4,8-triphenyl-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3,4,8-tris(4-methoxyphenyl)-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3-(3-bromo-4-chloro-2-(trifluoromethyl)quinolin-8-yl)benzonitrile
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3-bromo-4-chloro-2-(trifluoromethyl)-8-(4-(trifluoromethyl)phenyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 3-bromo-4-chloro-8-(thiophen-3-yl)-2-(trifluoromethyl)quinoline
0.1
-
 above, pH 9.5, 37°C, NPP3 Homo sapiens 4-chloro-3,8-diphenyl-2-(trifluoromethyl)quinoline