N-(3-methoxyphenyl)quinazolin-4-amine

Potent inhibitor of Epidermal growth factor receptor erbB1 with IC₅₀ = 842 nM.

OTAVAchemicals Catalogue Number:   7011830583

CAS Registry Number:  N/A

Purity: 97%

Ref.: Rewcastle et al.  Tyrosine Kinase Inhibitors.  5.  Synthesis and Structure-Activity Relationships  for 4-[(Phenylmethyl)amino]-  and 4-(Phenylamino)quinazolines  as Potent Adenosine 5'-Triphosphate Binding Site Inhibitors of the Tyrosine Kinase Domain of the Epidermal Growth Factor Receptor J. Med. Chem. (1996), 38,  3482-3487

Abstract: A series of 4-substituted quinazolines and related compounds  have been prepared and evaluated for their ability to inhibit the tyrosine kinase activity of the epidermal growth factor receptor on a phospholipase C-gamma 1-derived substrate. The results  show a narrow structure-activity relationship (SAR)  for the basic ring system, with quinazoline being the  preferred chromophore and benzylamino and anilino the preferred side chains.  In the 4-anilino  series, substitution on the 3-position of the phenyl ring with small  lipophilic electron-withdrawing groups provided analogues with enhanced potency.  Two series of compounds  [4-(phenylmethyl)amino and 4-(3-bromophenyl)amino] were studied  to determine SAFb for quinazoline substituents.  In  the more active  4-(3-bromophenyl)amino series,  electron-donating  groups  (NH₂, OMe)  at  the  6-  or 7-position  increased activity, in a pattern consistent with a requirement  for high electron density in the vicinity of  the 8-position of  the quinazoline ring.  The 6,7-dimethoxy derivatives were the most effective  in both series, with the 4-(3-bromophenyl)amino derivative (3)  having an IC₅₀ of  0.029 nM, making it by  far the most potent reported inhibitor  of  the tyrosine kinase activity of  the epidermal growth factor receptor  enzyme.

Need more information regarding this product? Send us an inquiry: Name: * First Last Company: * E-mail: (if you do not receive a response within 24 hours, please check your email spam folder, as it may have been blocked by your spam filter) * Please specify name of the product: * Word Verification: type_submit_reset_7 SubmitReset