104968-03-8

Basic information

• Product Name: 4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde
• Synonyms: 4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde
• CAS NO: 104968-03-8
• Molecular Formula: C₉H₆N₂O₂
• Molecular Weight: 174.158
• Mol File: 104968-03-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.4g/cm³
• Refractive Index: 1.675
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde(104968-03-8)
• EPA Substance Registry System: 4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde(104968-03-8)

Safety Data

• Hazardous Substances Data: 104968-03-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6N2O2/c12-5-8-10-7-4-2-1-3-6(7)9(13)11-8/h1-5H,(H,10,11,13)

Upstream product

• 1769-24-0 2-methyl-4-quinazolone 
• 118-92-3 anthranilic acid 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 84-26-4 rutaecarpine 
• 491-36-1 4-Hydroxyquinazoline 
• 725254-20-6 2-(2-quinolinyl)-3-hydroquinazolin-4-one 

Relevant articles and documents

Synthesis and evaluation of chalcone analogues containing a 4-oxoquinazolin-2-yl group as potential anti-tumor agents

The chalcone motif can be found in many molecules that contribute to essential biological processes, and many chalcone-containing compounds exhibit potent anti-cancer activity. Here, we synthesized two series of chalcone analogues (3a?s and 6a?s) based on substituting the chalcone B-ring or A-ring with a 4-oxoquinazolin-2-yl group, and then evaluated them for cytotoxic activity in human colorectal HCT-116 and breast cancer MCF-7 cell lines. Compounds 3a?s (in which a 4-oxoquinazolin-2-yl group functioned as the B-ring) were markedly more cytotoxic than compounds 6a?s (in which 4-oxoquinazolin-2-yl group functioned as the A-ring), based on their IC50 values to inhibit proliferation. Compound 3f was found as the most potent among 38 analogues and the mechanism of its cytotoxicity was investigated. Flow cytometry indicated that HCT-116 cells treated with compound 3f resulted in a dose-dependent accumulation of cells in the sub-G1 phase, which is representative of apoptotic cells. Subsequent assays (including Annexin V-FITC/PI, AO-EB, MitoSOX Red and JC-1 staining) confirmed that 3f exposure induced apoptosis in HCT-116 cells. Immunoblotting analysis indicated that cellular exposure to 3f increased the cleavage of PARP1 and caspases 3, 7, and 9. Taken together, this novel chalcone analogue has a cytotoxic effect on cultured cancer cell-lines that is likely mediated by inducing apoptosis via the mitochondrial death pathway.