60288-19-9

Basic information

• Product Name: 2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE
• Synonyms: 2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE
• CAS NO: 60288-19-9
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 60288-19-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE(60288-19-9)
• EPA Substance Registry System: 2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE(60288-19-9)

Safety Data

• Hazardous Substances Data: 60288-19-9(Hazardous Substances Data)

Usage

General Description

2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE is a chemical compound with the molecular formula C11H11NO2. It is a natural product found in plants of the Poaceae family, particularly in maize and wheat. It has been identified as a potent anti-fungal and allelopathic compound, which means it has an inhibitory effect on the growth of other plants. Its biological activity has also been studied for its potential as an anti-cancer and anti-inflammatory agent. Additionally, 2,5-DIMETHYL-3,1-BENZOXAZIN-4-ONE has been investigated for its role in pest resistance and has shown promise as a natural pesticide.

Upstream product

• 4389-50-8 2-amino-6-methylbenzoic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 147006-56-2 2,5-dimethylquinazolin-4(3H)-one 
• 147006-57-3 4-chloro-2,5-dimethylquinazoline 

Relevant articles and documents

Benzoxazin-4-ones as novel, easily accessible inhibitors for rhomboid proteases

Rhomboid proteases form one of the most widespread intramembrane protease families. They have been implicated in variety of human diseases. The currently reported rhomboid inhibitors display some selectivity, but their construction involves multistep synthesis protocols. Here, we report benzoxazin-4-ones as novel inhibitors of rhomboid proteases with a covalent, but slow reversible inhibition mechanism. Benzoxazin-4-ones can be synthesized from anthranilic acid derivatives in a one-step synthesis, making them easily accessible. We demonstrate that an alkoxy substituent at the 2-position is crucial for potency and results in low micromolar inhibitors of rhomboid proteases. Hence, we expect that these compounds will allow rapid synthesis and optimization of inhibitors of rhomboids from different organisms.

Synthesis, structure-activity relationships, and biological profiles of a quinazolinone class of histamine H3 receptor inverse agonists

A new series of quinazolinone derivatives was synthesized and evaluated as nonimidazole H3 receptor inverse agonists. 2-Methyl-3-(4-{[3-(1- pyrrolidinyl)propyl]oxy}phenyl)-5-(trifluoromethyl)-4(3H)-quinazolinone (1) was identified as a promising derivative for further evaluation following optimization of key parameters. Compound 1 has potent H3 inverse agonist activity and excellent selectivity over other histamine receptor subtypes and a panel of 115 unrelated diverse binding sites. Compound 1 also shows satisfactory pharmacokinetic profiles and brain penetrability in laboratory animals. Two hours after oral administration of 30 mg/kg of 1 to SD rats, significant elevation of brain histamine levels was observed where the brain H3 receptor was highly occupied (>90%). On the basis of species differences in P-glycoprotein (P-gp) susceptibility of 1 between human and rodent P-gps, the observed rodent brain permeability of 1 is significantly limited by P-gp mediated efflux in rodents, whereas the extent of P-gp mediated efflux in humans should be very small or negligible. The potential of 1 to be an efficacious drug was demonstrated by its excellent brain penetrability and receptor occupancy in P-gp-deficient CF-1 mice.