557770-89-5

Basic information

• Product Name: 7-(3-HYDROXY-PROPOXY)-3H-QUINAZOLIN-4-ONE
• Synonyms: 7-(3-HYDROXY-PROPOXY)-3H-QUINAZOLIN-4-ONE;7-(3-HYDORY-PROPOXY)-3H-QUINAZOLIN-4-ONE;4(3H)-Quinazolinone, 7-(3-hydroxypropoxy)-;7-(3-Hydroxypropoxy)-3,4-dihydroquinazolin-4-one;7-(3-Hydroxypropoxy)quinazolin-4-ol;7-(3-Hydroxypropoxy)-4(3H)-quinazolinone
• CAS NO: 557770-89-5
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 557770-89-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 491.5°C at 760 mmHg
• Flash Point: 251.1°C
• Appearance: /
• Density: 1.34
• Vapor Pressure: 1.77E-10mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 7-(3-HYDROXY-PROPOXY)-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(3-HYDROXY-PROPOXY)-3H-QUINAZOLIN-4-ONE(557770-89-5)
• EPA Substance Registry System: 7-(3-HYDROXY-PROPOXY)-3H-QUINAZOLIN-4-ONE(557770-89-5)

Safety Data

• Hazardous Substances Data: 557770-89-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 557770-89-5 differently. You can refer to the following data:
1. 7-(3-HYDROXY-PROPOXY)-3H-QUINAZOLIN-4-ONE is a substituted quinazolin-4(3H)-one that is used as an intermediate in the preparation of the aurora kinase inhibitor AZD1152 (A808100).
2. 7-(3-Hydroxypropoxy)-4(3H)-quinazolinone is a substituted quinazolin-4(3H)-one that is used as an intermediate in the preparation of the aurora kinase inhibitor AZD1152 (A808100).

InChI:InChI=1/C11H12N2O3/c14-4-1-5-16-8-2-3-9-10(6-8)12-7-13-11(9)15/h2-3,6-7,14H,1,4-5H2,(H,12,13,15)

Upstream product

• 446-32-2 4-fluoroanthranilic acid 
• 16499-57-3 7-fluoro-3H-quinazolin-4-one 
• 504-63-2 trimethyleneglycol 
• 16499-57-3 7-fluoro-1H-quinazolin-4-one 

Downstream Products

• 557770-90-8 4-chloro-7-(3-chloropropoxy)quinazoline 
• 1253969-55-9 C₂₇H₂₄ClN₇O 
• 1253969-34-4 C₃₁H₃₂N₈O₂ 
• 1253969-35-5 C₃₂H₃₄N₈O 
• 1253969-36-6 C₃₁H₃₄N₈O 
• 1253969-37-7 C₃₁H₃₂N₈O 

Relevant articles and documents

Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of aurora B kinase

The Aurora kinases have been the subject of considerable interest as targets for the development of new anticancer agents. While evidence suggests inhibition of Aurora B kinase gives rise to the more pronounced antiproliferative phenotype, the most clinically advanced agents reported to date typically inhibit both Aurora A and B. We have discovered a series of pyrazoloquinazolines, some of which show greater than 1000-fold selectivity for Aurora B over Aurora A kinase activity, in recombinant enzyme assays. These compounds have been designed for parenteral administration and achieve high levels of solubility by virtue of their ability to be delivered as readily activated phosphate derivatives. The prodrugs are comprehensively converted to the des-phosphate form in vivo, and the active species have advantageous pharmacokinetic properties and safety pharmacology profiles. The compounds display striking in vivo activity, and compound 5 (AZD1152) has been selected for clinical evaluation and is currently in phase 1 clinical trials.

Discovery of 4-aminoquinazoline - Urea derivatives as Aurora kinase inhibitors with antiproliferative activity

Two series of 20 novel 4-aminoquinazoline - urea derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro antiproliferative activity against six human cancer cell lines (K562, U937, A549, NCI-H661, HT29 and LoVo) using the MTT-based assay. Most compounds showed significant antiproliferative activities against four solid tumor cell lines, but no or poor activities against two leukemia cell lines. Furthermore, the target compounds were screened for Aurora A/B kinases inhibitory activity. Among them, 7c, 7d, 8c, and 8d are more potent against Aurora A kinase than ZM447439. Docking study of compounds 7d and ZM447439 revealed that they bound strongly to the ATP-binding sites of Aurora A and B. Thus, they may be promising lead compounds for the development of novel anti-tumor drug potentially via inhibiting Aurora kinases.

PROCESS AND INTERMEDIATE

The invention relates to a new process useful in the preparation of pharmaceutical compounds such as 2-{ethyl[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)propyl]amino}ethyl dihydrogen phosphate (AZD1152) and intermediates used therein.