18731-19-6

Basic information

• Product Name: 2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE
• Synonyms: 2,6-DIMETHYL-3H-QUINAZOLINE-4-ONE;2,6-Dimethyl-4(1H)-quinazolinone;2,6-DiMethylquinazolin-4(1H)-one;2,6-Dimethyl-4(3H)-quinazolinone;Raltitrexed Impurity 2
• CAS NO: 18731-19-6
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Mol File: 18731-19-6.mol
• Article Data: 20

Chemical Properties

• Melting Point: 330 °C
• Boiling Point: 336.6 °C at 760 mmHg
• Flash Point: 157.4 °C
• Appearance: /
• Density: 1.23 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.97±0.20(Predicted)
• CAS DataBase Reference: 2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE(18731-19-6)
• EPA Substance Registry System: 2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE(18731-19-6)

Safety Data

• Hazardous Substances Data: 18731-19-6(Hazardous Substances Data)

Usage

General Description

2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE is a chemical compound with a quinazoline ring structure and two methyl groups attached to the 2 and 6 positions. It is commonly used as a building block in the synthesis of pharmaceuticals and organic compounds. 2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE has been studied for its potential biological and pharmacological activities, including its antitumor and antibacterial properties. Additionally, 2,6-DIMETHYLQUINAZOLIN-4(3H)-ONE has been investigated for its potential use as a fluorescent probe in analytical chemistry. Overall, this chemical compound has diverse applications in the field of medicinal chemistry and drug discovery.

Upstream product

• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 108-24-7 acetic anhydride 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 1397833-57-6 (2-amino-5-methylphenyl) (1H-benzotriazole-1-yl)methanone 
• 78-39-7 Triethyl orthoacetate 
• 40545-33-3 2-amino-5-methylbenzamide 
• 123-54-6 acetylacetone 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 124-42-5 acetamidine hydrochloride 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 
• 1224442-42-5 C₁₀H₁₁N₃O₃ 
• 62175-49-9 2-methyl-6-methyl-4H-3,1-benzoxazin-4-one 
• 62-55-5 thioacetamide 
• 67081-68-9 2-acetamido-5-methylbenzoic acid 

Downstream Products

• 1123685-05-1 2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazolin-4(3H)-one 
• 1429782-21-7 4-chloro-6-methyl-2-methyl-quinazoline 

Relevant articles and documents

Improved synthesis of 3,4-dihydro-2,6-dimethyl-4-oxoquinazoline

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Quinazolin-4(3H)-one-Based Hydroxamic Acids: Design, Synthesis and Evaluation of Histone Deacetylase Inhibitory Effects and Cytotoxicity

The present article describes the synthesis and biological activity of various series of novel hydroxamic acids incorporating quinazolin-4(3H)-ones as novel small molecules targeting histone deacetylases. Biological evaluation showed that these hydroxamic acids were potently cytotoxic against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI?H23, lung). Most compounds displayed superior cytotoxicity than SAHA (suberoylanilide hydroxamic acid, Vorinostat) in term of cytotoxicity. Especially, N-hydroxy-7-(7-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5b) and N-hydroxy-7-(6-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5c) (IC50 values, 0.10–0.16 μm) were found to be approximately 30-fold more cytotoxic than SAHA (IC50 values of 3.29–3.67 μm). N-Hydroxy-7-(4-oxoquinazolin-3(4H)-yl)heptanamide (5a; IC50 values of 0.21–0.38 μm) was approximately 10- to 15-fold more potent than SAHA in cytotoxicity assay. These compounds also showed comparable HDAC inhibition potency with IC50 values in sub-micromolar ranges. Molecular docking experiments indicated that most compounds, as represented by 5b and 5c, strictly bound to HDAC2 at the active binding site with binding affinities much higher than that of SAHA.

One-pot synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones utilizing N-(2-aminobenzoyl)benzotriazoles

A convenient and efficient method has emerged for the one-pot synthesis of substituted quinazolin-4(3H)ones and nonaromatic alkaloids. 2-Substituted quinazolin-4(3H)-ones, 2,3-disubstituted quinazolin-4(3H)-ones, and 2,3-dihydroquinazolin-4(1H)-ones were obtained at yields of 46% to 95% by a one-pot reaction of N-(2-aminobenzoyl) benzotriazoles with amines and orthoesters or aldehydes under catalyst-free conditions.