100818-54-0

Basic information

• Product Name: N-Benzylquinazoline-4-amine
• Synonyms: 4-(Benzylamino)quinazoline;N-Benzylquinazoline-4-amine
• CAS NO: 100818-54-0
• Molecular Formula: C₁₅H₁₃N₃
• Molecular Weight: 235.289
• Mol File: 100818-54-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Benzylquinazoline-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylquinazoline-4-amine(100818-54-0)
• EPA Substance Registry System: N-Benzylquinazoline-4-amine(100818-54-0)

Safety Data

• Hazardous Substances Data: 100818-54-0(Hazardous Substances Data)

Upstream product

• 491-36-1 4-Hydroxyquinazoline 
• 100-46-9 benzylamine 
• 1885-29-6 anthranilic acid nitrile 
• 36185-83-8 N'-(2-cyanophenyl)-N,N-dimethylimidoformamide 
• 1276665-99-6 C₈H₅Cl₅N₅OP₃ 
• 15018-66-3 4-Aminoquinazoline 
• 253-82-7 quinazoline 
• 95862-54-7 1-Phenyl-2-(quinazolin-4-ylamino)-ethanone; hydrobromide 
• 5190-68-1 4-chloroquinazoline 

Relevant articles and documents

C-N bond formation by the oxidative alkylamination of azines: Comparison of AgPy2MnO4 versus KMnO4 as oxidant

Reports on the successful oxidative alkylamination of azines by the S NH-reaction, with the use of alkylamines other than methylamine, are very scarce. Hitherto, the experimental limitation to extend oxidative animation of azines wit

One-pot synthesis of 4-aminoquinazolines by hexamethyldisilazane-mediated reaction of quinazolin-4(3h)-ones with amines

Hexamethyldisilazane-mediated reaction of quinazolin-4(3H)-ones with primary amines led to facile formation of 4-aminoquinazolines through tandem silylation and substitution in a single pot. Excellent yields of the products (83-97%) and environmental friendliness (avoiding the use of chlorination reagents) are the advantages of this method. Copyright Taylor & Francis Group, LLC.

S(+)-4-(1-phenylethylamino)quinazolines as inhibitors of human immunoglobuline E synthesis: Potency is dictated by stereochemistry and atomic point charges at N-1

Since the pathogenesis of allergic diseases is associated with elevated levels of immunoglobulin E (IgE), we developed a high throughput reporter gene assay in a human B-cell line to screen for low molecular weight IgE inhibitory compounds. Monitoring the IL-4 driven IgE-germline promoter activity (IgE-GLP), we discovered 4-(1-phenylethylamino)qinazolines as potent inhibitors of IgE-germline gene expression. Testing of the individual enantiomers (1, 2) revealed that only the S(+) enantiomer 1 was active. A cell viability assay done in the same cell line in parallel discriminated the dose-dependent inhibition from a general antiproliferative effect. The observed correlation of the inhibitory potencies found in the reporter gene assay with those measured by IgE-ELISA in primary human splenocytes provided evidence that the blockade of IgE synthesis is the direct consequence of IgE-germline gene inhibition, thereby validating the reporter gene assay. Parallel synthesis in solution rapidly provided a series of analogues of compound I with modifications in the phenethylamine side chain and the quinazoline core for SAR studies. Increasing the lipophilicity of the arylalkylamine moiety yielded S(+)-4-(1-(2-naphthyl)ethylamino)quinazoline (6) as the most potent inhibitor (IC50 of 14 nM) while the R(-) enantiomer was again found to be inactive. Within the set of S enantiomers, quantum mechanical calculations revealed that the IgE inhibitory activity can be quantitatively described by the charge at N-1 of the heterocyclic core and to a lesser extent by the molar refractivity. These results demonstrate the importance of electron-deficient fused 4-aminopyrimidines and lipophilic side chains for biological activity. The strong preference for the S configuration of the phenethylamine side chain is remarkable insofar as biological activity for fused 4-(1-phenylethylamino)pyrimidines has been published for the R enantiomers only (EGFR tyrosine kinase inhibition).