| Identification | Back Directory | [Name]
PD158780 | [CAS]
171179-06-9 | [Synonyms]
PD 158780 solution
PD 158780; PD-158780
InSolution? PD 158780
PD 158780 - CAS 171179-06-9 - Calbiochem
InSolution PD 158780 - CAS 171179-06-9 - Calbiochem
N4-(3-Bromophenyl)-N6-methyl-pyrido[3,4-d]pyrimidine-4,6-diamine
Pyrido[3,4-d]pyriMidine-4,6-diaMine,N4-(3-broMophenyl)-N6-Methyl-
Pyrido[3,4-d]pyriMidine-4,6-diaMine,N4-(3-broMophenyl)-N6-Methyl- (Related Reference) | [Molecular Formula]
C14H12BrN5 | [MDL Number]
MFCD00942160 | [MOL File]
171179-06-9.mol | [Molecular Weight]
330.188 |
| Chemical Properties | Back Directory | [Melting point ]
174.0 to 178.0 °C | [Boiling point ]
499.6±45.0 °C(Predicted) | [density ]
1.611±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: ≥20mg/mL | [form ]
Yellow solid | [pka]
5.80±0.30(Predicted) | [color ]
yellow | [InChI]
1S/C14H12BrN5/c1-16-13-6-11-12(7-17-13)18-8-19-14(11)20-10-4-2-3-9(15)5-10/h2-8H,1H3,(H,16,17)(H,18,19,20) | [InChIKey]
KFHMLBXBRCITHF-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Uses]
PD 158780 is a potent tyrosine kinase inhibitor of the epidermal growth factor receptor and has been shown to delay substantial growth of tumors in vivo tumor models. | [Definition]
ChEBI: PD158780 is a pyridopyrimidine that is pyrido[3,4-d]pyrimidine-4,6-diamine in which the amino groups at positions 4 and 6 are substituted by a m-bromophenyl group and a methyl group, respectively. It is a potent, cell-permeable, reversible ATP-competitive inhibitor of EGFR tyrosine kinase activity [IC50 values of 0.008, 49 and 52 nM for EGFR, ErbB2 (HER2) and Erb4 (HER4)]. It does not inhibit FGF or PDGF-mediated tyrosine phosphorylation. Induces G1 cell cycle arrest in MCF10A cells and is antiproliferative in A431 human epidermal carcinoma cells. It has a role as an antineoplastic agent and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It is a pyridopyrimidine, a secondary amino compound, a member of bromobenzenes, a diamine and an aromatic amine. | [General Description]
A potent inhibitor of the EGFR tyrosine kinase activity (8 pM). Also inhibits heregulin-stimulated autophosphorylation in SK-BR-3 (IC50 =49 nM) and MDA-MB-453 (IC50 = 52 nM) breast carcinomas. The inhibition is competitive and results from binding of the inhibitor at the ATP site of the enzymes. Inhibits the LPA-stimulated MAP kinase kinase 1/2 (MKK1/2) activation and EGFR tyrosine phosphorylation in HeLa and NIH3T3 cells. | [Biological Activity]
Potent inhibitor of ErbB receptor family tyrosine kinases (IC 50 values are 0.008, 49 and 52 nM for EGFR, ErbB2 and ErbB2/ErbB4 respectively) that does not inhibit FGF or PDGF-mediated tyrosine phosphorylation. Induces G 1 cell cycle arrest in MCF10A cells and is antiproliferative in A431 human epidermal carcinoma cells. | [Biochem/physiol Actions]
Cell permeable: yes | [Synthesis]
Example 60: Synthesis of N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine
N-(3-Bromophenyl)-6-fluoro-pyrido[3,4-D]pyrimidin-4-amine (0.20 g, 0.63 mmol) was placed in a pressure vessel and an ethanol solution of methylamine was added and reacted at 100 °C. After completion of the reaction, purification was carried out by alumina column chromatography with the eluent dichloromethane/methanol (99:1, v/v) to afford the target product N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine (0.07 g, 34% yield).
1H NMR (DMSO) δ 9.69 (1H, s), 8.75 (1H, s), 8.41 (1H, s), 8.21 (1H, brs), 7.93 (1H, brd, J = 7.6 Hz), 7.41-7.28 (2H, m), 7.06 (1H, s), 6.82 (1H, q, J = 5.0 Hz), 4.95 ( 3H, d, J = 5.0 Hz). | [storage]
Store at -20°C | [References]
[1] Patent: US5654307, 1997, A |
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SynAsst Chemical.
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LETOPHARM LIMITED
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Sigma-Aldrich
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D&C Chemicals
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BePharm Ltd
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