62175-49-9

Basic information

• Product Name: 2,6-dimethyl-4H-3,1-benzoxazin-4-one
• Synonyms: 2,6-dimethyl-4H-3,1-benzoxazin-4-one;2,6-DIMETHYL-4H-BENZO[D][1,3]OXAZIN-4-ONE
• CAS NO: 62175-49-9
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 62175-49-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 125-126℃
• Appearance: /
• Density: 1.22
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,6-dimethyl-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dimethyl-4H-3,1-benzoxazin-4-one(62175-49-9)
• EPA Substance Registry System: 2,6-dimethyl-4H-3,1-benzoxazin-4-one(62175-49-9)

Safety Data

• Hazardous Substances Data: 62175-49-9(Hazardous Substances Data)

Usage

General Description

2,6-dimethyl-4H-3,1-benzoxazin-4-one, also known as DIMBOA, is a naturally occurring chemical compound found in various plants, such as maize and wheat. It belongs to the class of benzoxazinoids, which are specialized metabolites involved in plant defense against herbivores and pathogens. DIMBOA has been shown to possess antifungal, antibacterial, and antiviral properties, and it also acts as a feeding deterrent against insect pests. Additionally, DIMBOA has potential applications in agriculture, as it has been studied for its role in crop protection and enhancement. Its diverse biological activities and natural abundance make DIMBOA a significant compound in the fields of plant biology and agricultural science.

Upstream product

• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 201230-82-2 carbon monoxide 
• 29289-13-2 2-iodo-4-methylaniline 
• 108-24-7 acetic anhydride 
• 78-39-7 Triethyl orthoacetate 
• 583-68-6 2-bromo-p-toluidine 
• 64-19-7 acetic acid 

Downstream Products

• 18731-19-6 3,4-dihydro-2,6-dimethyl-4-oxoquinazoline 
• 1237744-74-9 4-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)benzoic acid 
• 1382052-27-8 6-amino-1-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile 
• 1382052-29-0 ethyl 2-amino-5-cyano-1-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)-6-oxo-4-phenyl-1,6-dihydropyridine-3-carboxylate 
• 1382052-37-0 4-amino-2,3-dihydro-N-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)-3-phenyl-2-thioxothiazole-5-carboxamide 
• 1382052-39-2 4-amino-N-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)-3-benzyl-2-thioxo-2,3-dihydrothiazole-5-carboxamide 
• 1382052-41-6 2-(2-phenylhydrazono)-2-cyano-N-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)acetamide 
• 1382052-43-8 2-(2-(4-aminosulphonylphenyl)hydrazono)-2-cyano-N-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)acetamide 
• 1382052-07-4 2-cyano-N-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)-3-phenylacrylamide 
• 1382052-09-6 C₂₁H₁₈N₄O₂ 
• 1382052-11-0 C₂₀H₁₅ClN₄O₂ 
• 1382052-13-2 C₂₀H₁₅N₅O₄ 
• 1382052-15-4 C₂₀H₁₆N₄O₃ 
• 1382052-17-6 C₂₀H₁₆N₄O₃ 

Relevant articles and documents

Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.

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.

Quinazoline-tyrphostin as a new class of antitumor agents, molecular properties prediction, synthesis and biological testing

A new series of substituted quinazolin-4-(3H)-one-tyrphostin derivatives was prepared and screened for their cytotoxic activity against three tumor cell lines, namely human breast cancer cell line (MCF-7), human cervical cancer cell line (HeLa) and human