18600-53-8

Basic information

• Product Name: 2-(4-BROMOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE
• Synonyms: 2-(4-BROMOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE;2-(4-BROMO-PHENYL)-BENZO[D][1,3]OXAZIN-4-ONE
• CAS NO: 18600-53-8
• Molecular Formula: C₁₄H₈BrNO₂
• Molecular Weight: 302.126
• Mol File: 18600-53-8.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-BROMOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE(18600-53-8)
• EPA Substance Registry System: 2-(4-BROMOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE(18600-53-8)

Safety Data

• Hazardous Substances Data: 18600-53-8(Hazardous Substances Data)

Usage

Chemical composition

Consists of a benzoxazinone core with a 4-bromophenyl substitution.

Physical state

Yellow solid.

Solubility

Soluble in organic solvents.

Pharmacological properties

Has potential as an anti-inflammatory agent and as a lead compound for drug development.

Molecular structure and properties

Promising for further research in medicinal chemistry and pharmaceutical science.

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Downstream Products

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Relevant articles and documents

Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N, N -diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.

C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range

Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.

Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation

A palladium-catalyzed chelation-assisted selective ortho C-H bond olefination of biologically active 4H-benzo[d][1,3] oxazin-4-one derivatives with activated olefins has been achieved. The products are obtained in good yields with high regio- and stereose