1145671-36-8

Basic information

• Product Name: 4-Chloroquinazoline-6,7-diol
• Synonyms: 4-Chloroquinazoline-6,7-diol
• CAS NO: 1145671-36-8
• Molecular Formula: C₈H₅ClN₂O₂
• Molecular Weight: 196.5905
• Mol File: 1145671-36-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 391.7±37.0 °C(Predicted)
• Appearance: /
• Density: 1.654±0.06 g/cm3(Predicted)
• PKA: 6.90±0.40(Predicted)
• CAS DataBase Reference: 4-Chloroquinazoline-6,7-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloroquinazoline-6,7-diol(1145671-36-8)
• EPA Substance Registry System: 4-Chloroquinazoline-6,7-diol(1145671-36-8)

Safety Data

• Hazardous Substances Data: 1145671-36-8(Hazardous Substances Data)

Usage

General Description

4-Chloroquinazoline-6,7-diol is a chemical compound with the molecular formula C8H6ClNO2. It is a quinazoline derivative that contains a chloro group and two hydroxyl groups. 4-Chloroquinazoline-6,7-diol has potential pharmaceutical applications due to its structural similarity to certain natural compounds and its potential as a drug candidate. It is being studied for its potential use in various therapeutic applications, including in the treatment of cancer and other diseases. 4-Chloroquinazoline-6,7-diol’s unique structure and potential pharmacological properties make it an interesting compound for further research and development in the pharmaceutical industry.

Upstream product

• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 938185-04-7 (7-acetoxy-4-chloro-quinazolin-6-yl) acetate 
• 765249-38-5 6,7-diacetoxy-4(3H)-quinazolinone 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 1174662-16-8 [7-(2,2-dimethylpropanoyloxy)-4-oxo-3H-quinazolin-6-yl] 2,2-dimethylpropanoate 
• 16064-15-6 6,7-dihydroxyquinazolin-4(3H)-one 
• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 
• 1145671-34-6 4-chloroquinazoline-6,7-diyl bis(2,2-dimethylpropanoate) 

Downstream Products

• 183322-18-1 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline 
• 1145671-38-0 4-chloro-7-hydroxyquinazolin-6-yl pivalate 

Relevant articles and documents

Development of a Potent Brain-Penetrant EGFR Tyrosine Kinase Inhibitor against Malignant Brain Tumors

The epidermal growth factor receptor (EGFR) is genetically altered in nearly 60% of glioblastoma tumors; however, tyrosine kinase inhibitors (TKIs) against EGFR have failed to show efficacy for patients with these lethal brain tumors. This failure is attributed to the inability of clinically tested EGFR TKIs to cross the blood-brain barrier (BBB) and achieve adequate pharmacological levels to inhibit various oncogenic forms of EGFR that drive glioblastoma. Through SAR analysis, we developed compound 5 (JCN037) from an anilinoquinazoline scaffold by ring fusion of the 6,7-dialkoxy groups to reduce the number of rotatable bonds and polar surface area and by introduction of an ortho-fluorine and meta-bromine on the aniline ring for improved potency and BBB penetration. Relative to the conventional EGFR TKIs erlotinib and lapatinib, JCN037 displayed potent activity against EGFR amplified/mutant patient-derived cell cultures, significant BBB penetration (2:1 brain-to-plasma ratio), and superior efficacy in an EGFR-driven orthotopic glioblastoma xenograft model.

Application of novel compound in preparing medicine for treating tumor

The invention discloses application of a compound as shown in the formula (I), a pharmaceutically acceptable salt or a solvent compound of the compound in preparing a medicine for treating tumor. In the formula, R1 is selected from formulae as shown in the description; R2 and R3 are respectively independently selected from H, halogen, alkyl and a formula as shown in the description; or R2 and R3 form a one-substituted or polysubstituted hexahydric aromatic heterocyclic ring with 1-2 heteroatoms together with carbon atoms connected with R2 and R3; R4, R5 and R6 respectively represent 0-3 substitution on a benzene ring; R4, R5 and R6 are respectively and independently selected from H, halogen atoms, C1-C6 alkyl, C1-C6 alkoxy, hydroxyl, amino, carboxyl, nitryl, CH3O(CH2)nCH2O- and a formula as shown in the description; and in the formula, n is an integer of 1-6. The compound disclosed by the invention is definite in medicinal effect when being used for treating tumor.

Three-point variation of a gefinitib quinazoline core

A versatile four-step process describing the controlled systematic variation of a key quinazoline core from one intermediate is highlighted.