| Identification | Back Directory | [Name]
PD 153035 HYDROCHLORIDE | [CAS]
153436-54-5 | [Synonyms]
PD153035HCl
Zinc00600292
PD 153035(AG-1517)
PD 153035 HYDROCHLORIDE
4-(3-Bromo-benzyl)-6,7-dimethoxy-quinazoline
4-(3-Bromphenylamino)-6,7-dimethylquinazoline
4-(3-Bromphenylamino)-6,7-bis(methoxy)quinazoline
N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine
4-Quinazolinamine, N-(3-bromphenyl)-6,7-dimethoxy-
4-[(3-BROMOPHENYL)AMINO]-6,7-DIMETHOXYQUINAZOLINE HYDROCHLORIDE | [Molecular Formula]
C16H15BrClN3O2 | [MDL Number]
MFCD01074805 | [MOL File]
153436-54-5.mol | [Molecular Weight]
396.67 |
| Chemical Properties | Back Directory | [Appearance]
Yellowish solid | [Melting point ]
189-190 °C | [Boiling point ]
472.1±45.0 °C(Predicted) | [density ]
1.499±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT | [solubility ]
Soluble in DMSO (up to 5 mg/ml). | [form ]
White to off-white solid. | [pka]
5.55±0.30(Predicted) | [color ]
White or off-white | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. | [InChI]
1S/C16H14BrN3O2/c1-21-14-7-12-13(8-15(14)22-2)18-9-19-16(12)20-11-5-3-4-10(17)6-11/h3-9H,1-2H3,(H,18,19,20) | [InChIKey]
LSPANGZZENHZNJ-UHFFFAOYSA-N | [SMILES]
Brc1cc(ccc1)Nc2ncnc3c2cc(c(c3)OC)OC |
| Hazard Information | Back Directory | [Chemical Properties]
Yellowish solid | [Uses]
PD153035 is an inhibitor of EGFR, competitive with ATP. EGF Receptor: IC50 = 25 pM (Ki = 6 pM). | [Definition]
ChEBI: A member of the class of quinazolines carrying a 3-bromophenylamino substituent at position 4 and two methoxy substituents at positions 6 and 7. | [Biological Activity]
An extremely potent inhibitor of epidermal growth factor (EGF) receptor tyrosine kinase, with an IC 50 of 25 pM. Inhibits other purified tyrosine kinases only at micromolar or higher concentrations. | [Description]
AG-1517 HCl (153436-54-5) is an ultra-potent inhibitor of epidermal growth factor receptor tyrosine kinase (EGFR), with an IC50 of 25 pM. Inhibits other tyrosine kinases at micromolar or higher concentrations. It selectively blocks EGF-mediated cellular processes including mitogenesis, early gene expression and oncogenic transformation.1?Inhibits the growth of a number of cancer cell lines.2?AG-1517 HCl is an extremely useful tool for exploring EGF-mediated cellular signaling.3 | [Synthesis]
GENERAL METHOD: 4-Chloro-6,7-dimethoxyquinazoline (1 mmol) was dissolved in refluxing 2-propanol (20 mL) and m-bromoaniline (1 mmol) was added dropwise. The reaction mixture was refluxed for 3-4 hours and the progress of the reaction was monitored by TLC until completion. Upon completion of the reaction, the precipitate was filtered out and washed sequentially with 2-propanol (10 mL) and ether (10 mL). If no precipitate formation was observed, the solvent was removed under reduced pressure to obtain a solid product. The final product was purified by recrystallization from 75% ethanol solution. | [target]
EGFR | [References]
1) Fry et al. (1994), A specific inhibitor of the epidermal growth factor receptor tyrosine kinase; Science, 265 1093
2) Bos et al. (1997), PD153035, a tyrosine kinase inhibitor, prevents epidermal growth factor receptor activation and inhibits growth of cancer cells in a receptor number-dependent manner; Clin. Cancer Res., 3 2099
3) Tetreault et al. (2008), Specific signaling cascades involved in cell spreading during healing of micro-wounded gastric epithelial monolayers; J. Cell. Biochem., 105 1240 |
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