17244-28-9

Basic information

• Product Name: 2-Acetyl-4(3H)-quinazolinone
• Synonyms: 2-Acetyl-4(3H)-quinazolinone;2-Acetylquinazolin-4(3H)-one
• CAS NO: 17244-28-9
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.1827
• Mol File: 17244-28-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 205 °C(Solv: ethanol (64-17-5))
• Boiling Point: 355.5°Cat760mmHg
• Flash Point: 168.8°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 3.1E-05mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: 2-8°C
• PKA: -2.25±0.20(Predicted)
• CAS DataBase Reference: 2-Acetyl-4(3H)-quinazolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetyl-4(3H)-quinazolinone(17244-28-9)
• EPA Substance Registry System: 2-Acetyl-4(3H)-quinazolinone(17244-28-9)

Safety Data

• Hazardous Substances Data: 17244-28-9(Hazardous Substances Data)

Usage

Molecular weight

208.19 g/mol
Heterocyclic compound with a quinazolin-4(3H)-one skeleton
Contains an acetyl group
Building block in organic compound synthesis
Used in pharmaceutical research
Potential applications in pharmaceutical and agrochemical synthesis

Potential biological activities

Different sources of media describe the Potential biological activities of 17244-28-9 differently. You can refer to the following data:
1. antifungal, anticancer, and anti-inflammatory properties

2. Antifungal, anticancer, anti-inflammatory

Synonyms

2-Acetyl-4-quinazolinone, 4-quinazolinone

Skeleton

Quinazolin-4(3H)-one

Functional group

Acetyl group

Uses

Building block in organic compound synthesis, pharmaceutical research

Potential applications

Synthesis of pharmaceuticals and agrochemicals

InChI:InChI=1/C10H8N2O2/c1-6(13)9-11-8-5-3-2-4-7(8)10(14)12-9/h2-5H,1H3,(H,11,12,14)

Upstream product

• 42599-89-3 (-)-(S)-2-(α-Hydroxyethyl)-4(3H)-quinazolinone 
• 101246-35-9 2-[2-Oxo-1-(triphenyl-λ⁵-phosphanylidene)-propylazo]-benzaldehyde 
• 103748-75-0 2-[2-Oxo-1-(triphenyl-λ⁵-phosphanylidene)-propyl]-1,2-dihydro-indazol-3-one 
• 491-36-1 4-Hydroxyquinazoline 
• 111-34-2 -butyl vinyl ether 
• 3137-64-2 2-ethyl-3H-quinazolin-4-one 
• 134-20-3 2-carbomethoxyaniline 
• 28144-70-9 anthranilic acid amide 
• 598-21-0 2-Bromoacetyl bromide 
• 331993-20-5 (+/-)-2-(2-methyl-2-oxazolidinyl)-4(3H)-quinazolinone 
• 18326-62-0 2-(2-oxopropanamido)benzamide 
• 127-17-3 2-oxo-propionic acid 
• 129768-47-4 2-(α,α-Dichloropropionyl)aminobenzamide 

Relevant articles and documents

Synthesis and biofilm inhibition studies of 2-(2-amino-6-arylpyrimidin-4-yl)quinazolin-4(3H)-ones

Synthesis of novel 4(3H)-quinazolinonyl aminopyrimidine derivatives has been achieved via quinazolinonyl enones which in turn were obtained from 2-acyl-4(3H)-quinazolinone. They have been assayed for biofilm inhibition against Gram-positive (methicillin-resistant Staphylococcus aureus (MRSA)) and Gram-negative bacteria (Acinetobacter baumannii). The analogues with 2,4,6-trimethoxy phenyl, 4-methylthio phenyl, and 3-bromo phenyl substituents (5h, 5j & 5k) have been shown to inhibit biofilm formation efficiently in MRSA with IC50 values of 20.7–22.4 μM). The analogues 5h and 5j have demonstrated low toxicity in human cells in vitro and can be investigated further as leads.

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.

Trapping of the putative cationic intermediate in the Morin rearrangement with carbon nucleophiles

This paper presents reactions in which the putative cationic intermediate in the Morin rearrangement is trapped by aromatic carbon nucleophiles (indoles and furans). For example, reaction of sulfoxide 27 with trifluoroacetic acid in chloroform provides, among other products, indole 29 and indoline 30. The indoline was shown to be in equilibrium with the nine-membered ring bridged indole 31. Other examples of Morin rearrangement-trapping reactions are presented, and mechanisms for these transformations are proposed.