5426-59-5

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1/C9H7BrN2O/c1-5-11-8-3-2-6(10)4-7(8)9(13)12-5/h2-4H,1H3,(H,11,12,13)

Upstream product

• 189634-99-9 2-acetylamino-5-bromo-benzonitrile 
• 108-24-7 acetic anhydride 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 19165-25-4 2-methyl-6-bromo-4H-3,1-benzoxazine-4-one 
• 60-35-5 acetamide 
• 21740-00-1 5-bromo-2-iodo-benzoic acid 
• 124-42-5 acetamidine hydrochloride 
• 28144-70-9 anthranilic acid amide 
• 78-39-7 Triethyl orthoacetate 
• 64-17-5 ethanol 
• 16313-66-9 5-bromoanthranilamide 
• 38985-79-4 5-bromo-N-acetylanthranilic acid 
• 610-71-9 2,5-dibromobenzoic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 

Downstream Products

• 75341-99-0 6-Bromo-2-[(E)-2-(4-hydroxy-3-nitro-phenyl)-vinyl]-3H-quinazolin-4-one 
• 75342-01-7 6-Bromo-2-[(E)-2-(3-nitro-phenyl)-vinyl]-3H-quinazolin-4-one 
• 75342-02-8 6-Bromo-2-[(E)-2-(4-methoxy-phenyl)-vinyl]-3H-quinazolin-4-one 
• 75341-97-8 6-Bromo-2-[(E)-2-(2-hydroxy-phenyl)-vinyl]-3H-quinazolin-4-one 
• 75342-00-6 6-Bromo-2-[(E)-2-(4-hydroxy-3-methoxy-phenyl)-vinyl]-3H-quinazolin-4-one 
• 474317-70-9 6-bromo-2-fluoren-9-ylidenemethyl-3H-quinazolin-4-one 
• 127033-32-3 (E)-6-bromo-2-styrylquinazolin-4(3H)-one 

Relevant academic research and scientific papers

Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions

A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.

Visible-light induced copper(i)-catalyzed oxidative cyclization of: O -aminobenzamides with methanol and ethanol via HAT

The use of the in situ generated ligand-copper superoxo complex absorbing light energy to activate the alpha C(sp3)-H of MeOH and EtOH via the hydrogen atom transfer (HAT) process for the synthesis of quinazolinones by oxidative cyclization of alcohols with o-aminobenzamide has been investigated. The synthetic utility of this protocol offers an efficient synthesis of a quinazolinone intermediate for erlotinb (anti-cancer agent) and 30 examples were reported.

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.

Novel Quinazolinone Inhibitors of ALK2 Flip between Alternate Binding Modes: Structure-Activity Relationship, Structural Characterization, Kinase Profiling, and Cellular Proof of Concept

Structure-activity relationship and crystallographic data revealed that quinazolinone-containing fragments flip between two distinct modes of binding to activin receptor-like kinase-2 (ALK2). We explored both binding modes to discover potent inhibitors and characterized the chemical modifications that triggered the flip in binding mode. We report kinase selectivity and demonstrate that compounds of this series modulate ALK2 in cancer cells. These inhibitors are attractive starting points for the discovery of more advanced ALK2 inhibitors.

Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues

A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope, mild reaction conditions, low environmental pollution, high atom-economy and good to excellent yields.

NOVEL BENZYLAMINO SUBSTITUTED QUINAZOLINES AND DERIVATIVES AS SOS1 INHIBITORS

The present invention encompasses compounds of formula (I), wherein the groups R1 to R7 have the meanings given in the claims and specification, their use as inhibitors of SOS1, pharmaceutical compositions which contain compounds of this kind and their use as medicaments/medical uses, especially as agents for treatment and/or prevention of oncological diseases.

Synthesis, biological evaluation and molecular docking studies of 6-Aryl-2-styrylquinazolin-4(3H)-ones

Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also evaluated against six Gram-positive and four Gram-negative bacteria, as well as two strains of fungi. Molecular docking studies (in silico) were conducted on compounds 5a, b, d and 6a, b, d-f to recognize the hypothetical binding motif of the title compounds within the active site of the dihydrofolate reductase and thymidylate synthase enzymes.

Synthesis and evaluation of quinazolines as inhibitors of the bacterial cell division protein FtsZ

The bacterial cell division protein FtsZ is one of many potential targets for the development of novel antibiotics. Recently, zantrin Z3 was shown to be a cross-species inhibitor of FtsZ; however, its specific interactions with the protein are still unknown. Herein we report the synthesis of analogues that contain a more tractable core structure and an analogue with single-digit micromolar inhibition of FtsZs GTPase activity, which represents the most potent inhibitor of Escherichia coli FtsZ reported to date. In addition, the zantrin Z3 core has been converted to two potential photo-cross-linking reagents for proteomic studies that could shed light on the molecular interactions between FtsZ and molecules related to zantrin Z3.

STYRYL QUINAZOLINE DERIVATIVES AS PHARMACEUTICALLY ACTIVE AGENTS

The present invention relates to styryl quinazoline derivatives of the general formula (I) and pharmaceutically acceptable solvates, hydrates, salts, regioisomeric and polymorphic forms thereof as well as pharmaceutical compositions containing at least on

Dicopper complexes catalyzed coupling/cyclization of 2-bromobenzoic acids with amidines leading to quinazolinones

Dicopper(I) complexes {Cu2(bpnp)(CH3CN) 4}(PF6)2] (2), [{Cu2(bpnp)(CH 3CN)4}(BAr4F)2] (3) and [Cu2(bpnp)Cl2] (4) were prepared from the complexation of [Cu(CH3CN)4](PF6) with 2,7-bis(2-pyridyl)-1,8- naphthyridine (bpnp) followed by anion metathesis and treatment of chloride sequentially. The X-ray structural analysis of 4 indicates the molecule to have a twofold axis passing through the Cu2Cl2 core, which has the shape of a butterfly, and that the Cu atom is tetrahedrally coordinated with in a Cl2N2 donor set. In preliminary experiments 2 was found to be an effective catalyst in the coupling/cyclization of 2-bromobenzoic acids with amidines, providing the corresponding quinazolinones in good yields. Copyright