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Literature summary for 2.7.10.2 extracted from

  • De Lucca, G.; Shi, Q.; Liu, Q.; Batt, D.; Beaudoin Bertrand, M.; Rampulla, R.; Mathur, A.; Discenza, L.; DArienzo, C.; Dai, J.; Obermeier, M.; Vickery, R.; Zhang, Y.; Yang, Z.; Marathe, P.; Tebben, A.; Muckelbauer, J.; Chang, C.; Zhang, H.; Gillooly, K.;
    Small molecule reversible inhibitors of Bruton's tyrosine kinase (BTK): structure-activity relationships leading to the identification of 7-(2-hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide (BMS-935177) (2016), J. Med. Chem., 59, 7915-7935.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
hanging drop vapor diffusion method, using 31% (w/v) methyl ether PEG 5000, 1% (w/v) PEG 8000, 0.2 M Tris-HCl, pH 8.5 Mus musculus

Inhibitors

Inhibitors Comment Organism Structure
4-(2-fluoro-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(isopropylamino)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(5-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(6-fluoro-1-oxoisoindolin-2-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(6-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(7-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
-
Mus musculus
4-(3-(8-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
-
Mus musculus
7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenyl)-9H-carbazole-1-carboxamide
-
Mus musculus
7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide
-
Mus musculus
7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(1-oxoisoquinolin-2(1H)-yl)phenyl)-9H-carbazole-1-carboxamide
-
Mus musculus
7-(2-hydroxypropan-2-yl)-4-(3-(4-oxoquinazolin-3(4H)-yl)-phenyl)-9H-carbazole-1-carboxamide
-
Mus musculus
7-(2-hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide BMS-935177 Mus musculus
7-(hydroxymethyl)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-carbazole-1-carboxamide
-
Mus musculus
ibrutinib
-
Mus musculus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + a [protein]-L-tyrosine Mus musculus
-
ADP + a [protein]-L-tyrosine phosphate
-
?

Organism

Organism UniProt Comment Textmining
Mus musculus P35991
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + a [protein]-L-tyrosine
-
Mus musculus ADP + a [protein]-L-tyrosine phosphate
-
?

Synonyms

Synonyms Comment Organism
Bruton's tyrosine kinase
-
Mus musculus
Btk
-
Mus musculus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000002
-
at pH 7.4 and 22°C Mus musculus 4-(3-(6-fluoro-1-oxoisoindolin-2-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
0.000002
-
at pH 7.4 and 22°C Mus musculus 4-(3-(7-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
0.000002
-
at pH 7.4 and 22°C Mus musculus 4-(3-(8-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
0.000003
-
at pH 7.4 and 22°C Mus musculus 7-(2-hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide
0.000003
-
at pH 7.4 and 22°C Mus musculus 7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenyl)-9H-carbazole-1-carboxamide
0.000003
-
at pH 7.4 and 22°C Mus musculus 7-(hydroxymethyl)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-carbazole-1-carboxamide
0.000004
-
at pH 7.4 and 22°C Mus musculus 4-(2-fluoro-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
0.000005
-
at pH 7.4 and 22°C Mus musculus 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
0.000005
-
at pH 7.4 and 22°C Mus musculus 4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
0.000005
-
at pH 7.4 and 22°C Mus musculus 7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide
0.000005
-
at pH 7.4 and 22°C Mus musculus 7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(1-oxoisoquinolin-2(1H)-yl)phenyl)-9H-carbazole-1-carboxamide
0.000005
-
at pH 7.4 and 22°C Mus musculus 4-(3-(5-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
0.000007
-
at pH 7.4 and 22°C Mus musculus 4-(3-(6-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide
0.000009
-
at pH 7.4 and 22°C Mus musculus 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
0.000011
-
at pH 7.4 and 22°C Mus musculus 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(isopropylamino)-9H-carbazole-1-carboxamide
0.000044
-
at pH 7.4 and 22°C Mus musculus 7-(2-hydroxypropan-2-yl)-4-(3-(4-oxoquinazolin-3(4H)-yl)-phenyl)-9H-carbazole-1-carboxamide