192217-99-5

Basic information

• Product Name: 4-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-
• CAS NO: 192217-99-5
• Molecular Formula: C15H12ClN3O
• Molecular Weight: 285.733
• Mol File: 192217-99-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-(192217-99-5)
• EPA Substance Registry System: 4-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-(192217-99-5)

Safety Data

• Hazardous Substances Data: 192217-99-5(Hazardous Substances Data)

Upstream product

• 86-96-4 1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 2242-77-5 N-carbamoylanthranilic acid methyl ester 
• 607-68-1 2,4-dichloroquinazoline 
• 104-94-9 4-methoxy-aniline 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 1251839-72-1 N-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)quinazolin-4-amine 

Relevant articles and documents

Design, synthesis and biological evaluation of 4-anilinoquinazoline derivatives as new c-myc G-quadruplex ligands

A series of 4-anilinoquinazoline derivatives were designed and synthesized as novel c-myc promoter G-quadruplex binding ligands. Subsequent biophysical and biochemical evaluation demonstrated that the introduction of aniline group at 4-position of quinazoline ring and two side chains with terminal amino group improved their binding affinity and stabilizing ability to G-quadruplex DNA. RT-PCR assay and Western blot showed that compound 7a could down-regulate transcription and expression of c-myc gene in Hela cells, which was consistent with the behavior of an effective G-quadruplex ligand targeting c-myc oncogene. More importantly, RTCA and colony formation assays indicated that 7a obviously inhibited Hela cells proliferation, without influence on normal primary cultured mouse mesangial cells. Flow cytometric assays suggested that 7a induced Hela cells to arrest in G0/G1 phase both in a time-dependent and dose-dependent manner.

Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold

Abstract A series of compounds with quinazoline scaffold were designed, synthesized and evaluated as novel potent 5-HT2A receptor ligands. N-(4-Chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine (5o) has a Ki value of 14.04 ± 0.21 nM, with a selectivity more than 10,000 fold over 5-HT1A receptors (D1 and D2-like receptors). The functional assay showed that this compound is an antagonist to 5-HT2A receptor with an IC50 value of 1.66 μM.

COMPOUNDS AND THERAPEUTICAL USE THEREOF

Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.