402855-01-0

Basic information

• Product Name: N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine
• Synonyms: N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine;N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)-4,6-quinazolinediamine
• CAS NO: 402855-01-0
• Molecular Formula: C₁₇H₁₆ClFN₄O₂
• Molecular Weight: 362.7859432
• Mol File: 402855-01-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine(402855-01-0)
• EPA Substance Registry System: N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine(402855-01-0)

Safety Data

• Hazardous Substances Data: 402855-01-0(Hazardous Substances Data)

Usage

Description

N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine is a quinazoline derivative characterized by a quinazoline core with a 3-chloro-4-fluorophenyl group and a 2-methoxyethoxy group attached. It is classified as a quinazoline-4,6-diamine, indicating the presence of two amine groups at positions 4 and 6 on the quinazoline ring. This chemical compound is of interest in medicinal chemistry and drug development due to the potential anticancer, anti-inflammatory, and antiproliferative properties associated with quinazoline derivatives.

Uses

Used in Pharmaceutical Industry:
N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine is used as a potential drug candidate for its potential anticancer properties. The presence of the 3-chloro-4-fluorophenyl group and the 2-methoxyethoxy group may enhance its biological activity and target specificity, making it a promising molecule for the development of new therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine is used as a compound of interest for studying its anti-inflammatory and antiproliferative properties. The unique structure of this quinazoline derivative allows researchers to explore its interactions with biological targets and evaluate its potential as a lead compound for the treatment of various diseases.
Used in Drug Development:
N4-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine is utilized in drug development as a starting point for the synthesis of new quinazoline-based drugs. Its structure can be modified to optimize its pharmacological properties, such as potency, selectivity, and bioavailability, leading to the discovery of novel therapeutic agents with improved efficacy and safety profiles.

Upstream product

• 53449-14-2 7-chloro-6-nitro-4(3H)-quinazolinone 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 1012057-59-8 4-chloro-7-(2-methoxyethoxy)-6-nitroquinazoline 
• 1012057-58-7 7-(2-methoxyethoxy)-6-nitro-4(3H)-quinazolinone 
• 31374-18-2 7-chloro-3,4-dihydroquinazolin-4-one 
• 446-32-2 4-fluoroanthranilic acid 
• 16499-57-3 7-fluoro-3H-quinazolin-4-one 
• 162012-70-6 4-chloro-7-fluoro-6-nitroquinazoline 
• 162012-69-3 7-fluoro-6-nitro-3H-quinazolin-4-one 
• 402855-06-5 N-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)-6-nitroquinazoline-4-amine 

Downstream Products

• 1012057-60-1 methyl 5-(4-(3-chloro-4-fluorophenylamino)-7-(2-methoxyethoxy)quinazolin-6-ylamino)-5-oxopentanoate 
• 1012057-61-2 methyl 6-(4-(3-chloro-4-fluorophenylamino)-7-(2-methoxyethoxy)quinazolin-6-ylamino)-6-oxohexanoate 
• 1402086-40-1 (E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(2-methoxyethoxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide 

Relevant articles and documents

6-Oxooxazolidine–quinazolines as noncovalent inhibitors with the potential to target mutant forms of EGFR

Despite the remarkable benefits of gefitinib, the clinical efficacy is eventually diminished due to the acquired point mutations in the EGFR (T790M). To address this unmet medical need, we demonstrated a strategy to prepare a hybrid analogue consisting of the oxooxazolidine ring and the quinazoline scaffold and provided alternative noncovalent inhibitors targeting mutant forms of EGFR. Most of the derivatives displayed moderate to good anti-proliferative activity against gefitinib-resistant NCI-H1975. Some of them exhibited potent EGFR kinase inhibitory activities, especially on EGFRT790Mand EGFRL858Rkinases. SAR studies led to the identification of a hit 9a that can target both of the most common EGFR mutants: L858R and T790M. Also, 9a displayed weaker inhibitory against cancer cell lines with low level of EGFR expression and good chemical stability under different pH conditions. The work presented herein showed the potential for developing noncovalent inhibitors targeting EGFR mutants.

Structure-activity study of quinazoline derivatives leading to the discovery of potent EGFR-T790M inhibitors

We have developed a series of 6, 7-disubstituted-4-(arylamino) quinazoline derivatives that functioned as irreversible EGFR inhibitors, and these compounds exhibited excellent enzyme inhibition potency. As compared with afatinib, some of them showed significantly enhanced activities towards H1975 cells (EGFR-T790M). Furthermore, the optimized compounds 7q and 8f also demonstrated good pharmacokinetic profiles, oral bioavailability as well as excellent in vivo efficacy in H1975 and HCC827 xenografts at a non-toxic dose. Based on the improved safety and efficacy against EGFR-T790M resistance, 7q and 8f are promising candidates for further studies.

6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL USES THEREOF

6-amino quinazoline or 3-cyano quinoline derivatives, preparation methods and pharmaceutical uses thereof are disclosed. Specifically, the present disclosure discloses novel 6-amino quinazoline or 3-cyano quinoline derivatives presented by general formula (I), or tautomers, enantiomers, diastereomers, racemates or pharmaceutically acceptable salts thereof, or metabolites, metabolic precursors or prodrugs thereof, and their uses as treatment agents especially as protein kinase inhibitors, in which each substitutent group of general formula (I) is as defined in the specification.