19165-25-4

Usage

Uses

Used in Pharmaceutical Research:
6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is used as a research compound for its antiviral, anti-inflammatory, and antimicrobial properties. Its unique structure and diverse potential applications make it an interesting target for further research and development in the pharmaceutical industry.
Used in Organic Synthesis:
In the field of organic synthesis, 6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is used as a key intermediate for the synthesis of various biologically active compounds. Its unique structure allows for the development of new pharmaceutical agents with improved therapeutic properties.
Used in Antiviral Applications:
6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is used as an antiviral agent, exhibiting potential activity against various viral infections. Its antiviral properties make it a promising candidate for the development of new antiviral drugs.
Used in Anti-inflammatory Applications:
6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is used as an anti-inflammatory agent, demonstrating potential to reduce inflammation and alleviate symptoms associated with inflammatory conditions. Its anti-inflammatory properties make it a valuable compound for the development of new therapeutic agents for inflammatory diseases.
Used in Antimicrobial Applications:
6-Bromo-2-methyl-4H-3,1-benzoxazin-4-one is used as an antimicrobial agent, showing potential activity against various microorganisms, including bacteria and fungi. Its antimicrobial properties make it a promising candidate for the development of new antimicrobial drugs to combat drug-resistant infections.

Upstream product

• 108-24-7 acetic anhydride 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 64-19-7 acetic acid 
• 38985-79-4 5-bromo-N-acetylanthranilic acid 
• 75-36-5 acetyl chloride 
• 78-39-7 Triethyl orthoacetate 
• 118-92-3 anthranilic acid 

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 
• 71822-73-6 6-bromo-3-phenyl-2-styryl-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 
• 4538-23-2 6-bromo-2-methyl-3-o-tolyl-3H-quinazolin-4-one 
• 98832-95-2 6-bromo-3-(o-chlorobenzoylamino)-2-methyl-4(3H)-quinazolone 
• 98832-97-4 N-(6-Bromo-2-methyl-4-oxo-4H-quinazolin-3-yl)-2-iodo-benzamide 
• 98832-96-3 6-bromo-3-(o-nitrobenzoylamino)-2-methyl-4(3H)-quinazolone 
• 77995-25-6 (4-{6-Bromo-2-[(E)-2-(2-hydroxy-phenyl)-vinyl]-4-oxo-4H-quinazolin-3-yl}-phenylsulfanyl)-acetic acid 
• 85226-52-4 6-Bromo-2-[(E)-2-(2-chloro-phenyl)-vinyl]-3-phenylamino-3H-quinazolin-4-one 
• 85226-42-2 2-(p-hydroxystyryl)-3-(p-nitroanilino)-6-bromo-4-(3H)-quinazolone 
• 85226-43-3 6-Bromo-2-[(E)-2-(4-methoxy-phenyl)-vinyl]-3-(4-nitro-phenylamino)-3H-quinazolin-4-one 

Relevant academic research and scientific papers

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

Quinazoline based 1,3,5-triazine derivatives as cancer inhibitors by impeding the phosphorylated RET tyrosine kinase pathway: Design, synthesis, docking, and QSAR study

The present research focused on designing a quinazoline skeleton, framed via 1,3,5-triazine derivatives (QBT) through field mapping and alignment studies. The QBT derivatives were synthesized via time- and cost-effective protocol. The 3D-QSAR study, computational physicochemical properties, and ADME calculation of the derivatives were performed to establish the affinity towards the biological system. Molecular docking in the adenosine triphosphate binding site of the RET tyrosine kinase domain (PDB ID: 7IVU) was studied to elucidate vital structural residues necessary for bioactivity. The derivatives were evaluated for anticancer potency against TPC-1 cells (thyroid cancer), MCF-7 cells (breast cancer), and one normal cell line (human foreskin fibroblasts) via 3-(4,5-dimethylthiazol-2-y1)-2,5-diphenyltetrazolium bromide assay followed by an in ovo CAM assay. The entire series of derivatives (8a–o) showed mild to significant anticancer potency against the selected cancer cell lines.

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 anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities of some 3H-quinazolin-4-one derivatives

Some new 3H-quinazolin-4-one derivatives were synthesised and screened for anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities. Compound 15d was more potent in reducing the cell viabilities of HT-29 and SW620 cells lines to 38%, 36.7%, compared to 5-FU which demonstrated cell viabilities of 65.9 and 42.7% respectively. The IC50 values of 15d were ～20?μg/ml. Assessment of apoptotic activity revealed that 15d decreased the cell viability by down regulating Bcl2 and BclxL. Moreover, compounds, 8j, 8d/15a/15e, 5b, and 8f displayed lowered IC50 values than oleanolic acid against proinflammatory isoforms of hGV, hG-X, NmPLA2, and AmPLA2. In addition, 8d, 8h, 8j, 15a, 15b, 15e, and 15f showed better anti-α-amylase than quercetin, whereas 8g, 8h, and 8i showed higher anti-α-glucosidase activity than allopurinol. Thus, these compounds can be considered as potential antidiabetic agents. Finally, none of the compounds showed higher antiproteases or xanthine oxidase activities than the used reference drugs.

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.

Discovery and development of extreme selective inhibitors of the ITD and D835Y mutant FLT3 kinases

Aberrant activation of FMS-like tyrosine receptor kinase 3 (FLT3) is implicated in the pathogenesis of acute myeloid leukemia (AML) in 20–30% of patients. In this study we identified a highly selective (phenylethenyl)quinazoline compound family as novel potent inhibitors of the FLT3-ITD and FLT3-D835Y kinases. Their prominent effects were confirmed by biochemical and cellular proliferation assays followed by mice xenograft studies. Our modelling experiments and the chemical structures of the compounds predict the possibility of covalent inhibition. The most effective compounds triggered apoptosis in FLT3-ITD AML cells but had either weak or no effect in FLT3-independent leukemic and non-leukemic cell lines. Our results strongly suggest that our compounds may become therapeutics in relapsing and refractory AML disease harboring various ITD and tyrosine kinase domain mutations, by their ability to overcome drug resistance.

Structure-Activity Relationship for the 4(3H)-Quinazolinone Antibacterials

We recently reported on the discovery of a novel antibacterial (2) with a 4(3H)-quinazolinone core. This discovery was made by in silico screening of 1.2 million compounds for binding to a penicillin-binding protein and the subsequent demonstration of antibacterial activity against Staphylococcus aureus. The first structure-activity relationship for this antibacterial scaffold is explored in this report with evaluation of 77 variants of the structural class. Eleven promising compounds were further evaluated for in vitro toxicity, pharmacokinetics, and efficacy in a mouse peritonitis model of infection, which led to the discovery of compound 27. This new quinazolinone has potent activity against methicillin-resistant (MRSA) strains, low clearance, oral bioavailability and shows efficacy in a mouse neutropenic thigh infection model.

Design and synthesis of quinazolinone tagged acridones as cytotoxic agents and their effects on EGFR tyrosine kinase

In a quest for finding potent cytotoxic molecules, we have designed and synthesized a new scaffold by tagging quinazolinones with an acridone moiety. The new acridone-4-carboximide derivatives were evaluated for their cytotoxic potentials against the MCF7 breast cancer cell line and three colon cancer cell lines (LS174T, SW1398, and WiDr). Compound 26 showed relatively potent cytotoxic activity among the derivatives, against all the cell lines tested. Mechanistic studies for the selected derivatives 7, 8, 16, 17, 25, and 26 were conducted through in vitro EGFR tyrosine kinase inhibition studies. The results indicate that compound 26 has a better EGFR tyrosine kinase inhibitory profile. The in vitro EGFR inhibition data was correlated with the cytotoxic properties, and molecular docking studies were performed with regard to the receptor autophosphorylation sites of the protein kinase domain of the EGFR.

Reactivity of 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3- d][1,3]oxazin-4-one under microwave irradiation conditions

The reactivity of variably substituted 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one towards carbon and oxygen nucleophiles under microwave irradiation conditions was investigated. Optimization of the reaction conditions of oxazinones with carbon nucleophiles led to the synthesis of a series of 4-hydroxy-quinolin-2-ones and 4-hydroxy-1,8-naphthyridin-2-ones in high yields, whereas reaction with a variety of alcohols proceeded smoothly to the formation of the corresponding N-acetyl-anthranilates and nicotinates.