N-(3-Chlorophenyl)-6,7-dimethoxy-4-quinazolinamine
Basic information
- CAS
175178-82-2- Standard SMILES
COc1cc2ncnc(Nc3cccc(Cl)c3)c2cc1OC- InChIKey
GFNNBHLJANVSQV-UHFFFAOYSA-N- Molecular formula
- C16H14ClN3O2
- Average molar mass
- 315.75 g/mol
Overview
Tyrphostin AG 1478 is a member of the class of quinazolines that is quinazoline substituted by methoxy groups at positions 6 and 7 and a (3-chlorophenyl)nitrilo group at position 4. It acts as an epidermal growth factor receptor antagonist. It has a role as a geroprotector, an antiviral agent, an antineoplastic agent and an epidermal growth factor receptor antagonist. It is an aromatic ether, a member of quinazolines and a member of monochlorobenzenes.
Names & identifiers
- Preferred name
- N-(3-Chlorophenyl)-6,7-dimethoxy-4-quinazolinamine
- IUPAC
- N-(3-chlorophenyl)-6,7-dimethoxyquinazolin-4-amine
- English name
- AG 1478
- Molecular formula
- C16H14ClN3O2
- Molecular weight
- 315.75
Names & synonyms
153436-53-4AG-14784-Quinazolinamine, N-(3-chlorophenyl)-6,7-dimethoxy-N-(3-Chlorophenyl)-6,7-dimethoxy-4-quinazolinamineAG-1478 free baseSUH0SEZ9HYNSC-693255(3-Chlorophenyl)(6,7-dimethoxyquinazolin-4-yl)amineRefChem:389357Tyrphostin AG 1478N-(3-chlorophenyl)-6,7-dimethoxyquinazolin-4-amine175178-82-2
Show more names
COMPOUND 32AG 1517SU 5271WHI-P 79NSC 669364PD-153,035Tyrphostin AGAG 1478 USP/EP/BP
Tyrphostin AG-1478AG 14784-(3-Chloroanilino)-6,7-dimethoxyquinazolineAG1478tyrphostin AG1478MFCD00270914AG-1478 (Tyrphostin AG-1478)DTXSID0051447
Database identifiers
- CAS
175178-82-2- ChEMBL
CHEMBL7917
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 56.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 360
Experimental & physicochemical properties
LogP3.51
Collision Cross Section177.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0051447]
Physicochemical properties
- Melting point
- 180 · 180 - 183°C
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 M · 0.1 M HCl: soluble <0.4 mg/mL
- form
- Pale yellow solid
- color
- Off-white
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
- InChI
- 1S/C16H14ClN3O2/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
- GFNNBHLJANVSQV-UHFFFAOYSA-N
- SMILES
- Clc1cc(ccc1)Nc2ncnc3c2cc(c(c3)OC)OC
- FDA UNII
- 62 B68RSL · TC62B68RSL
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
DescriptionAG-1478 (175478-82-2; base) is a potent and selective inhibitor of the EGFR kinase (IC50 = 3 nM). Inhibits proliferation of a variety human cancer cell lines.1,2 AG-1478 reduces pulmonary fibrosis in a rat model.3Cell permeable.
UsesTyrphostin AG 1478 has been used as epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor to study its effect on desmoid cell mobility in boyden chamber motility assays. It has also been used to inhibit phosphorylation of c-Met by exogenous transforming growth factor α in epidermoid carcinoma cell line A431.
UsesA highly potent and specific EGFR tyrosine kinase inhibitor with an IC50 of 3 nM.
UsesTyrphostin AG 1478 is a potent and selective inhibitor of EGFR.
General DescriptionHighly potent and specific inhibitor of the epidermal growth factor (EGF) receptor tyrosine kinase (IC50 = 3 nM). Much higher concentrations are required for inhibition of the kinase activity of the closely related HER2 (neu/erb-B2) receptor (IC50 >100 μM), the platelet-derived growth factor (PDGF) receptor (IC50 >100 μM), and p210Bcr-Abl (IC50 >50 μM). Its mechanism of inhibition likely mimics that of the related compound, 4-(3-chloroanilino)quinazoline (CAQ), a competitive inhibitor with respect to ATP.
Additional notes
DefinitionChEBI: Tyrphostin AG 1478 is a member of the class of quinazolines that is quinazoline substituted by methoxy groups at positions 6 and 7 and a (3-chlorophenyl)nitrilo group at position 4. It acts as an epidermal growth factor receptor antagonist. It has a role as an epidermal growth factor receptor antagonist, an antineoplastic agent, a geroprotector and an antiviral agent. It is a member of quinazolines, an aromatic ether and a member of monochlorobenzenes.
Related reactions
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Compound notes
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