19165-25-4

Basic information

• Product Name: 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one
• Synonyms: 6-BROMO-2-METHYL-4H-3,1-BENZOXAZIN-4-ONE;6-BROMO-2-METHYL-4H-BENZO[D][1,3]OXAZIN-4-ONE;6-BroMo-2-Methyl-benzo[d][1,3]oxazin-4-one
• CAS NO: 19165-25-4
• Molecular Formula: C₉H₆BrNO₂
• Molecular Weight: 240.05
• Mol File: 19165-25-4.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 352°Cat760mmHg
• Flash Point: 166.7°C
• Appearance: /
• Density: 1.7g/cm³
• Sensitive: Air Sensitive
• CAS DataBase Reference: 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one(19165-25-4)
• EPA Substance Registry System: 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one(19165-25-4)

Safety Data

• Hazardous Substances Data: 19165-25-4(Hazardous Substances Data)

Usage

General Description

6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is a chemical compound with a molecular formula C9H6BrNO2. It belongs to the class of benzoxazinones and is a derivative of 2-methyl-4H-3,1-benzoxazin-4-one. 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is commonly used in organic synthesis and pharmaceutical research due to its potential biological activities. 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one has been studied for its antiviral, anti-inflammatory, and antimicrobial properties, making it a versatile compound in medicinal chemistry. Its unique structure and diverse potential applications make it an interesting target for further research and development in various fields of science and industry.

Upstream product

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Downstream Products

• 38985-79-4 5-bromo-N-acetylanthranilic acid 
• 130862-74-7 [4-(6-bromo-2-methyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonyl]-guanidine 
• 792924-51-7 (2-amino-5-bromo-phenyl)-(4-butyl-phenyl)-methanone 
• 439868-51-6 N-[4-bromo-2-(3-pyridinylcarbonyl)phenyl]-acetamide 
• 24295-50-9 4-(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid 
• 4538-23-2 6-bromo-2-methyl-3-o-tolyl-3H-quinazolin-4-one 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 89-52-1 o-acetylamino-benzoic acid 
• 34801-09-7 N-(2-aminophenyl)acetamide 
• 71822-73-6 6-bromo-3-phenyl-2-styryl-3H-quinazolin-4-one 

Relevant articles and documents

Quinazoline clubbed 1,3,5-triazine derivatives as VEGFR2 kinase inhibitors: design, synthesis, docking, in vitro cytotoxicity and in ovo antiangiogenic activity

Abstract: A series of quinazoline clubbed 1,3,5-triazine derivatives (QCT) were synthesized and evaluated for their in vitro anticancer activity against HeLa (human cervical cancer), MCF-7 (human breast cancer cell), HL-60 (human promyelocytic leukemia cell), HepG2 (human Hepatocellular carcinoma cell), and one normal cell line HFF (human foreskin fibroblasts). In vitro assay result encouraged to further move towards in ovo anticancer evaluation using chick embryo. The series of QCT derivatives showed higher anticancer and antiangiogenic activity against HeLa and MCF-7 cell lines. In the series, synthetic molecule 8d, 8l, and 8m displayed significant activity. Further, these results substantiated by docking study on VGFR2. SAR study concluded that the potency of drugs depends on the nature of aliphatic substitution and the heterocyclic ring system. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis, antiviral and cytotoxic activity of 6-bromo-2,3-disubstituted-4(3H)-quinazolinones.

In the present study, a series of 6-bromo-2,3-disubstitued-4(3H)-quinazolinones was synthesized by condensation of 6-bromo-2-substituted-benzoxazin-4-one with trimethoprim, pyrimethamine and lamotrigine. The chemical structures of the synthesized compound

Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C–O Bond Formation

Enantioselective Cu-catalyzed C–O cross coupling reactions yielding atropisomeric resorcinol-bearing quinazolinones have been developed. Utilizing a new guanidinylated dimeric peptidic ligand, a set of products were generated in good yields with excellent

Synthesis and evaluation of new quinazolin-4(3H)-one derivatives as potent antibacterial agents against multidrug resistant Staphylococcus aureus and Mycobacterium tuberculosis

Staphylococcus aureus and Mycobacterium tuberculosis are major causative agents responsible for serious nosocomial and community-acquired infections impacting healthcare systems globally. Over several decades, these pathogens have developed resistance to multiple antibiotics significantly affecting morbidity and mortality. Thus, these recalcitrant pathogens are amongst the most formidable microbial pathogens for which international healthcare agencies have mandated active identification and development of new antibacterial agents for chemotherapeutic intervention. In our present work, a series of new quinazolin-4(3H)-one derivatives were designed, synthesized and evaluated for their antibacterial activity against ESKAP pathogens and pathogenic mycobacteria. The experiments revealed that 4'c, 4'e, 4'f and 4'h displayed selective and potent inhibitory activity against Staphylococcus aureus with MIC values ranging from 0.03-0.25 μg/mL. Furthermore, compounds 4'c and 4'e were found to be benign to Vero cells (CC50 = >5 μg/mL) and displayed promising selectivity index (SI) > 167 and > 83.4 respectively. Additionally, 4'c and 4'e demonstrated equipotent MIC against multiple drug-resistant strains of S. aureus including VRSA, concentration dependent bactericidal activity against S. aureus and synergized with FDA approved drugs. Moreover, compound 4′c exhibited more potent activity in reducing the biofilm and exhibited a PAE of ～2 h at 10X MIC which is comparable to levofloxacin and vancomycin. In vivo efficacy of 4'c in murine neutropenic thigh infection model revealed that 4'c caused a similar reduction in cfu as vancomycin. Gratifyingly, compounds 4d, 4e, 9a, 9b, 14a, 4'e and 4'f also exhibited anti-mycobacterial activity with MIC values in the range of 2-16 μg/mL. In addition, the compounds were found to be less toxic to Vero cells (CC50 = 12.5->100 μg/mL), thus displaying a favourable selectivity index. The interesting results obtained here suggest the potential utilization of these new quinazolin-4(3H)-one derivatives as promising antibacterial agents for treating MDR-Staphylococcal and mycobacterial infections.