32084-59-6

Basic information

• Product Name: 6-Bromoquinazolin-4-ol
• Synonyms: 6-Bromoquinazolin-4(3H)-one;6-Bromo-3,4-dihydro-4-oxoquinazoline 98%;6-Bromo-4-hydroxyquinazoline;6-bromo-4-quinazolinone;6-Bromoquinazolin-4-ol;6-bromo-4(3h)-quinazolinone;6-Bromoquinazolin-4(3H)-one 98%;6-bromoquinazolin-4(3H)-one(SALTDATA: FREE)
• CAS NO: 32084-59-6
• Molecular Formula: C₈H₅BrN₂O
• Molecular Weight: 225.04
• Product Categories: blocks;Heterocycles;Quinolines
• Mol File: 32084-59-6.mol

Chemical Properties

• Melting Point: 131-132 °C
• Boiling Point: 374.2 °C at 760 mmHg
• Flash Point: 180.1 °C
• Appearance: /
• Density: 1.82 g/cm³
• Vapor Pressure: 8.51E-06mmHg at 25°C
• Refractive Index: 1.72
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.05±0.20(Predicted)
• CAS DataBase Reference: 6-Bromoquinazolin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoquinazolin-4-ol(32084-59-6)
• EPA Substance Registry System: 6-Bromoquinazolin-4-ol(32084-59-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 32084-59-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C8H5BrN2O/c9-5-1-2-7-6(3-5)8(12)11-4-10-7/h1-4H,(H,10,11,12)

Upstream product

• 77287-34-4 formamide 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 64-18-6 formic acid 
• 491-36-1 4-Hydroxyquinazoline 
• 20353-93-9 Gold's reagent 
• 6313-33-3 formamidine hydrochloride 
• 16313-66-9 5-bromoanthranilamide 
• 149-73-5 trimethyl orthoformate 
• 4692-98-2 5-bromoisatoic anhydride 
• 3473-63-0 formamidine acetic acid 
• 195457-53-5 6-bromo-4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride salt 
• 39263-32-6 2-amino-5-bromobenzonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 63243-76-5 2-amino-5-bromobenzoic acid,ethyl ester 

Downstream Products

• 38267-96-8 6-bromo-4-chloroquinozoline 
• 75341-91-2 6-Bromo-3-(p-tolylamino-methyl)-3H-quinazolin-4-one 
• 75341-92-3 6-Bromo-3-[(4-chloro-phenylamino)-methyl]-3H-quinazolin-4-one 
• 75341-95-6 6-Bromo-3-[(4-methoxy-phenylamino)-methyl]-3H-quinazolin-4-one 
• 75341-90-1 6-Bromo-3-phenylaminomethyl-3H-quinazolin-4-one 
• 75341-94-5 6-Bromo-3-[(4-ethoxy-phenylamino)-methyl]-3H-quinazolin-4-one 
• 75341-93-4 4-[(6-Bromo-4-oxo-4H-quinazolin-3-ylmethyl)-amino]-benzoic acid ethyl ester 
• 75341-96-7 6-Bromo-3-[(4-bromo-phenylamino)-methyl]-3H-quinazolin-4-one 
• 49681-96-1 6-Bromo-2-mercapto-3,4-dihydrochinazolin-4-on 
• 544461-20-3 6-bromo-4(3H)-quinazolinethione 
• 677298-22-5 6-(2-chloro-6-methoxyphenyl)-3H-quinazolin-4-one 
• 677298-23-6 6-(2,4,6-trimethylphenyl)-3H-quinazolin-4-one 
• 307538-42-7 SMER28 
• 1005010-01-4 4-chloro-6-(3,4-dimethoxy-phenyl)-quinazoline 

Relevant articles and documents

Design and synthesis of novel 6-aryl substituted 4-anilinequinazoline derivatives as potential PI3Kδ inhibitors

In this study, a series of new 6-aryl substituted 4-anilinequinazolines was designed and synthesized as PI3Kδ inhibitors based on our reported chemical structures. The preliminary structure-activity relationship (SAR) was established, and compounds 13h an

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

Photo-Triggered Self-Induced Homolytic Dechlorinative Sulfonylation/Cyclization of Unactivated Alkenes: Synthesis of Quinazolinones Containing a Sulfonyl Group

A self-photocatalyzed sulfonylation/cyclization of quinazolinones containing unactivated alkenes with various sulfonyl chlorides was developed. The protocol provides access to sulfonyl radicals via energy transfer from the quinazolinone skeleton to the sulfonyl chloride. Notably, the transformations proceeded without any external photocatalysts, additives, or oxidants, providing an alternative method for fabricating sulfonylated compounds.

Electrosynthesis of CF3-Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene

An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF3 source is described. A variety of polycyclic quinazolinones were successfully synthesized in 52–81% yields under transition metal- and oxidant-free conditions. The Langlois reagent used in this strategy as a CF3 reagent possesses the advantages of bench-stablity, cost-effectivity and high-efficiency. Additionally, gram-scale reaction, broad substrate scope and good functional group tolerance demonstrated the synthetic usefulness of this protocol.

Visible-Light Photosynthesis of CHF2/CClF2/CBrF2-Substituted Ring-fused Quinazolinones in Dimethyl Carbonate

With eco-friendly and sustainable CO2-derived dimethyl carbonate as the sole solvent, the visible-light-induced cascade radical reactions have been established as a green and efficient tool for constructing various CHF2/CClF2/CBrF2-substituted ring-fused quinazolinones.

Discovery of BPR1R024, an Orally Active and Selective CSF1R Inhibitor that Exhibits Antitumor and Immunomodulatory Activity in a Murine Colon Tumor Model

Colony-stimulating factor-1 receptor (CSF1R) is implicated in tumor-associated macrophage (TAM) repolarization and has emerged as a promising target for cancer immunotherapy. Herein, we describe the discovery of orally active and selective CSF1R inhibitors by property-driven optimization of BPR1K871 (9), our clinical multitargeting kinase inhibitor. Molecular docking revealed an additional nonclassical hydrogen-bonding (NCHB) interaction between the unique 7-aminoquinazoline scaffold and the CSF1R hinge region, contributing to CSF1R potency enhancement. Structural studies of CSF1R and Aurora kinase B (AURB) demonstrated the differences in their back pockets, which inspired the use of a chain extension strategy to diminish the AURA/B activities. A lead compound BPR1R024 (12) exhibited potent CSF1R activity (IC50 = 0.53 nM) and specifically inhibited protumor M2-like macrophage survival with a minimal effect on antitumor M1-like macrophage growth. In vivo, oral administration of 12 mesylate delayed the MC38 murine colon tumor growth and reversed the immunosuppressive tumor microenvironment with the increased M1/M2 ratio.

Novel (Z)-N'-(2-oxoindolin-3-ylidene)-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides and an anticancer composition comprising the same as an active ingredient

(Z)- N' - (2-oxoindolin -3 - ylidene) -2 - (4-oxoquinazolin -3 (4H) - yl) acetohydrazide and an anticancer composition containing the same as an active ingredient. , It will be described below. (Z)- N' - (2-oxoindoline -3 - ylidene) -2 - (4-oxazoline -3 (4H) - yl) acetohydrazide according to the present invention activates procacaspase -3 to promote the conversion to caspase -3, so that it can be used as a proliferation inhibitor for various cancer cells. The compound according to the present invention can be developed as an active ingredient of a potent anticancer agent.

Design, synthesis, and biological evaluation of novel 6-(pyridin-3-yl) quinazolin-4(3H)-one derivatives as potential anticancer agents via PI3K inhibition

Abnormal activation of the PI3K/Akt pathway is demonstrated in most of human malignant tumors via regulation of proliferation, cell cycle, and apoptosis. Therefore, drug discovery and development of targeting the PI3K/Akt pathway has attracted great interest of researchers in the development of anticancer drugs. In this study, fifteen 6-(pyridin-3-yl) quinazolin-4(3H)-one derivatives were designed and synthesized. Anticancer activities of the synthetic compounds were evaluated and the potential mechanisms were explored. Several compounds showed certain proliferation inhibitory activity against the tested cancer cells including human non-small cell lung cancer (NSCLC) HCC827, human neuroblastoma SH-SY5Y and hepatocellular carcinoma LM3 cells. Among them, compound 7i and 7m showed the best inhibitory activity against all the cancer cell lines and more active against HCC827 cells with IC50 values of 1.12 μM and 1.20 μM, respectively. In addition, 7i and 7m showed lower inhibitory activity against H7702 cells (human normal liver cells) with IC50 values of 8.66 μM and 10.89 μM, respectively, nearly 8-fold lower than that in HCC827 cells. These results suggested that compounds 7i and 7m had certain selectivity to tumor cells, compared to human normal cells. Further biological studies indicated 7i induced G2/M phase arrests and cell apoptosis of HCC827 cells via PI3K/Akt and caspase dependent pathway. Together, these novel 6-(pyridin-3-yl) quinazolin-4(3H)-one derivatives such as compound 7i and 7m might be lead compounds for development of potential anti-cancer drugs.

6 - (Pyridin -3 -yl) quinazoline -4 (3H) - ketone derivative as well as preparation and application thereof

The invention discloses 6 - (pyridin -3 -yl) quinazoline -4 (3H) - ketone derivatives, and the structural formula is shown I. The invention also discloses a synthetic method thereof. Anti-tumor activity studies found compounds Ii and Im for human non-small cell lung cancer (NSCLC) HCC827. Human erythrocytes and leukocyte leukemia cells HEL, human neuroblastoma SH-SY5Y and liver cancer LM3 cells all show good proliferation inhibition activity. Ia-Iq all 17 compounds can reverse the drug resistance of Tylin drug-resistant A549/T cells, adriamycin drug-resistant MCF F F F F-7/ADR cells and adriamycin resistance HepG2/ADM cells to the corresponding chemotherapeutic drugs in different degrees.

Pyrido imidazole substituted quinazolinone derivative as well as synthesis method and application thereof

The invention discloses a pyridazole substituted quinazolinone derivative, and the structural formula thereof is as follows. The invention also discloses a synthetic method thereof. The pyrido-imidazole-substituted quinazolinone derivative can induce high