7253-22-7

Basic information

• Product Name: 4,6-Dichloroquinazoline
• Synonyms: 4,6-DICHLOROQUINAZOLINE;6-dichloroquinazoline
• CAS NO: 7253-22-7
• Molecular Formula: C₈H₄Cl₂N₂
• Molecular Weight: 199.04
• Product Categories: Halides;Heterocycles
• Mol File: 7253-22-7.mol
• Article Data: 21

Chemical Properties

• Melting Point: 155-156 °C
• Boiling Point: 305.7 °C at 760 mmHg
• Flash Point: 167.3 °C
• Appearance: /
• Density: 1.486 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.11±0.30(Predicted)
• CAS DataBase Reference: 4,6-Dichloroquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dichloroquinazoline(7253-22-7)
• EPA Substance Registry System: 4,6-Dichloroquinazoline(7253-22-7)

Safety Data

• Hazardous Substances Data: 7253-22-7(Hazardous Substances Data)

Usage

General Description

4,6-Dichloroquinazoline is a chemical compound with the molecular formula C8H4Cl2N2. It is a colorless solid that is insoluble in water but soluble in organic solvents. 4,6-Dichloroquinazoline is primarily used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is also a precursor in the production of specialized compounds for research and development purposes. This chemical has potential applications in the field of medicinal chemistry and drug discovery due to its unique structure and reactivity. However, it is important to handle 4,6-Dichloroquinazoline with care, as it may pose risks to human health and the environment if not properly managed.

Upstream product

• 16064-14-5 6-chloroquinazolin-4-one 
• 16064-14-5 6-chloro-4-hydroxyquinazoline 
• 77287-34-4 formamide 
• 635-21-2 5-chloroanthranilic acid 
• 5202-85-7 2-Amino-5-chlorobenzamide 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 118-92-3 anthranilic acid 
• 16064-14-5 6-chloroquinazolin-4-one 

Downstream Products

• 7505-75-1 4-ethoxy-6-chloro-quinazoline 
• 6637-19-0 N-(6-chloro-quinazolin-4-yl)-ethylenediamine 
• 150450-53-6 4-[[3,4-(methylenedioxy)benzyl]amino]-6-chloroquinazoline 
• 188569-30-4 6-chloro-4-methoxyquinazoline 
• 474710-50-4 ethyl 4-(6-chloroquinazolin-4-yl)-2-fluorobenzoate 

Relevant articles and documents

Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity

A series of novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether moieties were designed and synthesized. Their anticancer activities were evaluated by MTT assay, the results showed that most compounds exhibited extremely inhibitory effects against hepatoma SMMC-7721 cells. In particular, compounds Q2 and Q8 displayed the more potent inhibitory activity with IC50 values of 0.64 and 0.63 μM, which were better than that of gemcitabine (1.40 μM). Further mechanism studies indicated that compounds Q2, Q8, Q13 and Q19 could control the migration of SMMC-7721 cells effectively, and inhibit the proliferation of cancer cells by inhibiting the DNA replication. Western-blot results showed that compounds Q2 and Q8 induced irreversible apoptosis of SMMC-7721 cells by regulating the expression level of apoptose-related proteins. Those studies demonstrated that the penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments merited further research as potential anticancer agents.

Design, synthesis, and anticancer activities of sodium quinazolin-4-diselenide compounds

Substituted 4-chloroquinazoline reacted with sodium diselenide to give novel sodium quinazoline-4-diselenide compounds. The reaction provides an efficient and facile approach to the synthesis of sodium quinazoline-4-diselenide compounds. Structures of title compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. MTT assay was adopted to show anticancer activities of the compounds. Compounds 5a and 5h showed good activities against cancer-cell lines MDA-MB-435, MDA-MB-231, A549, SiHa, and HeLa. In addition, 5a exhibited quite good anticancer effects on relative above cell lines with 10μM concentration compared with oxaliplatin and gefitinib of the commercial anticancer drugs.

Discovery of SP-96, the first non-ATP-competitive Aurora Kinase B inhibitor, for reduced myelosuppression

Aurora Kinase B is a serine-threonine kinase known to be overexpressed in several cancers, with no inhibitors approved for clinical use. Herein, we present the discovery and optimization of a series of novel quinazoline-based Aurora Kinase B inhibitors. The lead inhibitor SP-96 shows sub-nanomolar potency in Aurora B enzymatic assays (IC50 = 0.316 ± 0.031 nM). We identified the important pharmacophore features resulting in selectivity against receptor tyrosine kinases. Particularly, SP-96 shows >2000 fold selectivity against FLT3 and KIT which is important for normal hematopoiesis. This could diminish the adverse effect of neutropenia reported in the clinical trials of the Aurora B inhibitor Barasertib, which inhibits FLT3 and KIT in addition to Aurora B. Enzyme kinetics of SP-96 shows non-ATP-competitive inhibition which makes it a first-in-class inhibitor. Further, SP-96 shows selective growth inhibition in NCI60 screening, including inhibition of MDA-MD-468, a Triple Negative Breast Cancer cell line.