361392-71-4

Basic information

• Product Name: 4-((S)-2-Methoxymethyl-pyrrolidin-1-yl)-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide
• Synonyms: 4-((S)-2-Methoxymethyl-pyrrolidin-1-yl)-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide
• CAS NO: 361392-71-4
• Molecular Weight: 494.391
• Mol File: 361392-71-4.mol

Chemical Properties

• CAS DataBase Reference: 4-((S)-2-Methoxymethyl-pyrrolidin-1-yl)-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((S)-2-Methoxymethyl-pyrrolidin-1-yl)-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide(361392-71-4)
• EPA Substance Registry System: 4-((S)-2-Methoxymethyl-pyrrolidin-1-yl)-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide(361392-71-4)

Safety Data

• Hazardous Substances Data: 361392-71-4(Hazardous Substances Data)

Upstream product

• 169205-78-1 6-amino-4-[(3-bromophenyl)amino]quinazoline 
• 63126-47-6 (2S)-2-(methoxymethyl)-1-pyrrolidine 

Relevant articles and documents

6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity

A series of new 6-substituted-4-(3-bromophenylamino)quinazoline derivatives that may function as irreversible inhibitors of epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases have been prepared. These inhibitors have, at the C-6 position, butynamide, crotonamide, and methacrylamide Michael acceptors bearing water-solublilizing substituents. These compounds were prepared by acylation of 6-amino-4-(3-bromophenylamino)quinazoline with unsaturated acid chlorides or mixed anhydrides. We show that attaching a basic functional group onto the Michael acceptor results in greater reactivity, due to intramolecular catalysis of the Michael addition and/or an inductive effect of the protonated basic group. This, along with improved water solubility, results in compounds with enhanced biological properties. We present molecular modeling and experimental evidence that these inhibitors interact covalently with the target enzymes. One compound, 16a, was shown to have excellent oral activity in a human epidermoid carcinoma (A431) xenograft model in nude mice.