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Literature summary extracted from

  • Xu, G.; Searle, L.L.; Hughes, T.V.; Beck, A.K.; Connolly, P.J.; Abad, M.C.; Neeper, M.P.; Struble, G.T.; Springer, B.A.; Emanuel, S.L.; Gruninger, R.H.; Pandey, N.; Adams, M.; Moreno-Mazza, S.; Fuentes-Pesquera, A.R.; Middleton, S.A.; Greenberger, L.M.
    Discovery of novel 4-amino-6-arylaminopyrimidine-5-carbaldehyde oximes as dual inhibitors of EGFR and ErbB-2 protein tyrosine kinases (2008), Bioorg. Med. Chem. Lett., 18, 3495-3499.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.7.10.1 drug development novel series of 4-aminopyrimidine-5-carbaldehyde oximes that are potent and selective inhibitors of both EGFR and ErbB-2 tyrosine kinases Homo sapiens

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.7.10.1 complex of 4-aminopyrimidine-5-carbaldehyde oxime with EGFR, at 2.3 A resolution. NH2 makes key hydrogen bonding interaction with backbone C=O of Met 793 Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.7.10.1 3-[[5-([6-amino-5-[(E)-(methoxyimino)methyl]pyrimidin-4-yl]amino)-1H-indazol-1-yl]methyl]benzonitrile
-
 Homo sapiens
2.7.10.1 4-amino-6-(1H-indazol-5-ylamino)pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-([3-chloro-4-[(3,5-difluorobenzyl)oxy]phenyl]amino)pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-([3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]amino)pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[(1-benzyl-1H-indazol-5-yl)amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[(3-bromophenyl)amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[(3-chloro-4-fluorobenzyl)amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[(3-chloro-4-fluorophenyl)amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-chlorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(1-methylethyl)oxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methoxybenzyl)oxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methoxyethyl)oxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methylpropyl)oxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-benzyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-ethyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde oxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-1H-indol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-fluorobenzyl)-2,3-dihydro-1H-indol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(3-methoxybenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[1-(4-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[2-(3-fluorobenzyl)-1H-benzimidazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-amino-6-[[4-(benzyloxy)-3-chlorophenyl]amino]pyrimidine-5-carbaldehyde O-methyloxime
-
 Homo sapiens
2.7.10.1 4-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]-6-(methylamino)pyrimidine-5-carbaldehyde O-methyloxime 39% inhibition of ErbB-2 at 0.01 mM; 48% inhibition of EGFR at 0.002 mM Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
2.7.10.1 Homo sapiens P00533
-
-
2.7.10.1 Homo sapiens P04626
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.7.10.1 BT-474 cell
-
 Homo sapiens
-
2.7.10.1 SK-BR-3 cell
-
 Homo sapiens
-

Synonyms

EC Number Synonyms Comment Organism
2.7.10.1 Egfr
-
 Homo sapiens
2.7.10.1 ErbB-1
-
 Homo sapiens
2.7.10.1 ErbB-2
-
 Homo sapiens
2.7.10.1 erbB2 receptor tyrosine kinase
-
 Homo sapiens
2.7.10.1 Her-2
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.7.10.1 0.000005
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-ethyloxime
2.7.10.1 0.000006
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methoxyethyl)oxime
2.7.10.1 0.000007
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-ethyloxime
2.7.10.1 0.000012
-
-
 Homo sapiens 4-amino-6-([3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]amino)pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000012
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde oxime
2.7.10.1 0.000013
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000014
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(1-methylethyl)oxime
2.7.10.1 0.000014
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methoxyethyl)oxime
2.7.10.1 0.000016
-
-
 Homo sapiens 4-amino-6-[[4-(benzyloxy)-3-chlorophenyl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000018
-
-
 Homo sapiens 4-amino-6-([3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]amino)pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.00002
-
-
 Homo sapiens 3-[[5-([6-amino-5-[(E)-(methoxyimino)methyl]pyrimidin-4-yl]amino)-1H-indazol-1-yl]methyl]benzonitrile
2.7.10.1 0.000022
-
-
 Homo sapiens 4-amino-6-[(1-benzyl-1H-indazol-5-yl)amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000023
-
-
 Homo sapiens 4-amino-6-[[1-(3-chlorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000023
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-benzyloxime
2.7.10.1 0.000025
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(1-methylethyl)oxime
2.7.10.1 0.000027
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.00003
-
-
 Homo sapiens 4-amino-6-[[1-(3-chlorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000032
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methylpropyl)oxime
2.7.10.1 0.000033
-
-
 Homo sapiens 4-amino-6-([3-chloro-4-[(3,5-difluorobenzyl)oxy]phenyl]amino)pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000042
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde oxime
2.7.10.1 0.000044
-
-
 Homo sapiens 3-[[5-([6-amino-5-[(E)-(methoxyimino)methyl]pyrimidin-4-yl]amino)-1H-indazol-1-yl]methyl]benzonitrile
2.7.10.1 0.000044
-
-
 Homo sapiens 4-amino-6-[(1-benzyl-1H-indazol-5-yl)amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000047
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methoxybenzyl)oxime
2.7.10.1 0.000048
-
-
 Homo sapiens 4-amino-6-[[2-(3-fluorobenzyl)-1H-benzimidazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000057
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-2,3-dihydro-1H-indol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000076
-
-
 Homo sapiens 4-amino-6-[[2-(3-fluorobenzyl)-1H-benzimidazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000095
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-benzyloxime
2.7.10.1 0.000104
-
-
 Homo sapiens 4-amino-6-[[1-(4-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000153
-
-
 Homo sapiens 4-amino-6-[[4-(benzyloxy)-3-chlorophenyl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000173
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methylpropyl)oxime
2.7.10.1 0.000189
-
-
 Homo sapiens 4-amino-6-[[1-(4-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000255
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-2,3-dihydro-1H-indol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000267
-
-
 Homo sapiens 4-amino-6-[[1-(3-methoxybenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000306
-
-
 Homo sapiens 4-amino-6-(1H-indazol-5-ylamino)pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.000435
-
-
 Homo sapiens 4-amino-6-[[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino]pyrimidine-5-carbaldehyde O-(2-methoxybenzyl)oxime
2.7.10.1 0.001123
-
-
 Homo sapiens 4-amino-6-[(3-chloro-4-fluorobenzyl)amino]pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.004123
-
-
 Homo sapiens 4-amino-6-(1H-indazol-5-ylamino)pyrimidine-5-carbaldehyde O-methyloxime
2.7.10.1 0.00522
-
-
 Homo sapiens 4-amino-6-[(3-chloro-4-fluorobenzyl)amino]pyrimidine-5-carbaldehyde O-methyloxime