26060-06-0

Basic information

• Product Name: 2-(2-THIENYL)-4H-3,1-BENZOXAZIN-4-ONE
• Synonyms: 2-(2-THIENYL)-4H-3,1-BENZOXAZIN-4-ONE;2-Thien-2-yl-4H-3,1-benzoxazin-4-one
• CAS NO: 26060-06-0
• Molecular Formula: C₁₂H₇NO₂S
• Molecular Weight: 229.25
• Mol File: 26060-06-0.mol
• Article Data: 20

Chemical Properties

• Melting Point: 142-143
• Boiling Point: 357.8 °C at 760 mmHg
• Flash Point: 170.2 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 2.66E-05mmHg at 25°C
• Refractive Index: 1.703
• PKA: 1.65±0.20(Predicted)
• CAS DataBase Reference: 2-(2-THIENYL)-4H-3,1-BENZOXAZIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-THIENYL)-4H-3,1-BENZOXAZIN-4-ONE(26060-06-0)
• EPA Substance Registry System: 2-(2-THIENYL)-4H-3,1-BENZOXAZIN-4-ONE(26060-06-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 26060-06-0(Hazardous Substances Data)

Usage

General Description

2-(2-thienyl)-4H-3,1-benzoxazin-4-one, also known as DIMBOA, is a natural chemical compound found in plants such as maize, wheat, and rye. It is a benzoxazinoid compound and is known for its role in plant defense against herbivores and pathogens. DIMBOA has been shown to have antifungal, antibacterial, and insecticidal properties and is thought to be involved in the resistance of plants to pests and diseases. Additionally, DIMBOA has been studied for its potential as a bioactive compound with various pharmacological activities, including antioxidant, antimicrobial, and anticancer properties.

InChI:InChI=1/C12H7NO2S/c14-12-8-4-1-2-5-9(8)13-11(15-12)10-6-3-7-16-10/h1-7H

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Downstream Products

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Relevant articles and documents

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

Silver-Mediated Synthesis of 4H-Benzoxazin-4-ones by Intramolecular Decarboxylative O-Acylation Reactions with α-Oxocarboxylic Acid

The first example of an intramolecular decarboxylative acylation reaction for the synthesis of 4H-benzoxazin-4-one derivatives has been described. The silver-mediated reaction has a broad substrate scope and provides a mild and rapid approach to the corre