194851-16-6

Basic information

• Product Name: 7-BROMO-1H-QUINAZOLIN-4-ONE
• Synonyms: 7-BroMoquinazolin-4-one;7-BroMo-3,4-dihydroquinaz...;7-Bromo-4-quinazolone;7-BroMoquinazolin-4(1H)-one;7-BroMo-3,4-dihydroquinazolin-4-one, 95+%;7-Bromo-3H-quinazolin-4-one;4(1H)-Quinazolinone, 7-bromo-;7-BROMO-1H-QUINAZOLIN-4-ONE
• CAS NO: 194851-16-6
• Molecular Formula: C₈H₅BrN₂O
• Molecular Weight: 225.04
• Product Categories: Halides;CHIRAL CHEMICALS;Fused Ring Systems
• Mol File: 194851-16-6.mol

Chemical Properties

• Boiling Point: 428.784 °C at 760 mmHg
• Flash Point: 213.121 °C
• Appearance: /
• Density: 1.822 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.36±0.20(Predicted)
• CAS DataBase Reference: 7-BROMO-1H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-1H-QUINAZOLIN-4-ONE(194851-16-6)
• EPA Substance Registry System: 7-BROMO-1H-QUINAZOLIN-4-ONE(194851-16-6)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 194851-16-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-BROMO-1H-QUINAZOLIN-4-ONE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential therapeutic properties. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Medicinal Chemistry Research:
As a building block in medicinal chemistry, 7-BROMO-1H-QUINAZOLIN-4-ONE is utilized for the design and synthesis of novel compounds with potential applications in treating various diseases and conditions. Its reactivity and structural features make it a versatile component in the creation of new chemical entities.
Used in Agrochemical Development:
7-BROMO-1H-QUINAZOLIN-4-ONE is employed as a starting material in the development of agrochemicals, such as pesticides and herbicides. Its chemical properties enable the creation of effective compounds for agricultural applications, contributing to crop protection and yield enhancement.
Used in Organic Synthesis:
7-BROMO-1H-QUINAZOLIN-4-ONE serves as a valuable precursor in organic synthesis, allowing for the formation of a wide range of chemical compounds. Its bromine atom and quinazolinone ring provide opportunities for further functionalization and modification, expanding the scope of synthetic chemistry.
Used in Antitumor Research:
7-BROMO-1H-QUINAZOLIN-4-ONE is studied for its potential as an antitumor agent, with ongoing research exploring its effects on various types of cancer. Its pharmacological properties and interactions with biological targets make it a promising candidate for the development of cancer therapies.
Used in Drug Discovery and Development:
In the field of drug discovery and development, 7-BROMO-1H-QUINAZOLIN-4-ONE is employed as a lead compound for the identification and optimization of new therapeutic agents. Its unique chemical features facilitate the exploration of novel drug targets and the advancement of innovative treatment options.

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

Upstream product

• 20776-50-5 2-amino-4-bromobenzoic acid 
• 77287-34-4 formamide 
• 112253-70-0 2-amino-4-bromobenzamide 
• 122-51-0 orthoformic acid triethyl ester 
• 3473-63-0 formamidine acetic acid 
• 109-94-4 formic acid ethyl ester 
• 194851-17-7 7-bromo-4-(3-chloro-4-fluoroanilino)quinazoline hydrochloride salt 
• 99277-71-1 4-bromo-2-nitrobenzoic acid 
• 67-56-1 methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 832114-32-6 7-Bromo-1-(4-methoxy-benzyl)-1H-quinazolin-4-one 
• 158580-57-5 methyl 4-bromo-2-nitrobenzoate 
• 1427534-38-0 methyl (E)-4-bromo-2-(((dimethylamino)methylene)amino)benzoate 

Downstream Products

• 573675-55-5 7-bromo-4-chloro-quinazoline 
• 887129-09-1 7-bromo-3-(2,4-dimethoxy-benzyl)-3H-quinazolin-4-one 
• 1312448-35-3 7-((4-fluorophenyl)ethynyl)quinazolin-4(3H)-one 
• 1334602-75-3 7-bromo-4-((4-methoxybenzyl)oxy)quinazoline 
• 1334602-76-4 4-(4-methoxybenzyloxy)-7-morpholin-4-yl-quinazoline 
• 1334602-74-2 4-(4-chloroquinazolin-7-yl)morpholine 
• 1334600-89-3 7-morpholin-4-yl-4-((S)-3-phenyl-piperidin-1-yl)-quinazoline 
• 1420990-58-4 C₂₁H₁₆F₂N₆O₂S 
• 1420990-50-6 3-benzyl-7-bromo-6-nitroquinazolin-4(3H)-one 
• 1420990-51-7 6-amino-3-benzyl-7-bromoquinazolin-4(3H)-one 
• 1420990-52-8 3-benzyl-7-bromo-6-[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]quinazolin-4(3H)-one 
• 1260769-84-3 7-bromo-4-chloro-6-nitroquinazoline 
• 451494-38-5 7-bromo-N⁴-(3-chloro-4-fluorophenyl)quinazoline-4,6-diamine 
• 858465-96-0 7-phenylquinazolin-4(3H)-one 

Relevant articles and documents

Development of Specific, Irreversible Inhibitors for a Receptor Tyrosine Kinase EphB3

Erythropoietin-producing human hepatocellular carcinoma (Eph) receptor tyrosine kinases (RTKs) regulate a variety of dynamic cellular events, including cell protrusion, migration, proliferation, and cell-fate determination. Small-molecule inhibitors of Eph kinases are valuable tools for dissecting the physiological and pathological roles of Eph. However, there is a lack of small-molecule inhibitors that are selective for individual Eph isoforms due to the high homology within the family. Herein, we report the development of the first potent and specific inhibitors of a single Eph isoform, EphB3. Through structural bioinformatic analysis, we identified a cysteine in the hinge region of the EphB3 kinase domain, a feature that is not shared with any other human kinases. We synthesized and characterized a series of electrophilic quinazolines to target this unique, reactive feature in EphB3. Some of the electrophilic quinazolines selectively and potently inhibited EphB3 both in vitro and in cells. Cocrystal structures of EphB3 in complex with two quinazolines confirmed the covalent linkage between the protein and the inhibitors. A "clickable" version of an optimized inhibitor was created and employed to verify specific target engagement in the whole proteome and to probe the extent and kinetics of target engagement of existing EphB3 inhibitors. Furthermore, we demonstrate that the autophosphorylation of EphB3 within the juxtamembrane region occurs in trans using a specific inhibitor. These exquisitely specific inhibitors will facilitate the dissection of EphB3's role in various biological processes and disease contribution.

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.

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.

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.

Design, synthesis, biological evaluation and structure-activity relationship study of quinazolin-4(3H)-one derivatives as novel USP7 inhibitors

Recent research has indicated that the abnormal expression of the deubiquitinase USP7 induces tumorigenesis via multiple cell pathways, and in particular, the p53-MDM2-USP7 pathway is well understood. USP7 is emerging as a promising target for cancer therapy. However, there are limited reports on USP7 inhibitors. Here we report design, synthesis and biological evaluation of novel quinazolin-4(3H)-one derivatives as potent USP7 inhibitors. Our results indicated that the compounds C9 and C19 exhibited the greatest potency against the USP7 catalytic domain, with IC50 values of 4.86 μM and 1.537 μM, respectively. Ub-AMC assays further confirmed IC50 values of 5.048 μM for C9 and 0.595 μM for C19. MTT assays indicated that gastric cancer MGC-803 cells were more sensitive to these compounds than BGC-823 cells. Flow cytometry analysis revealed that C9 restricted cancer cell growth at the G0/G1 and S phases and inhibited the proliferation and clone formation of MGC-803 cells. Further biochemical experiments indicated that C9 decreased the MDM2 protein level and increased the levels of the tumour suppressors p53 and p21 in a dose-dependent manner. Docking studies predicted that solvent exposure of the side chains of C9 and C19 would uniquely form hydrogen bonds with Met407 of USP7. Additionally, C9 exhibited a remarkable anticancer effect in a zebrafish gastric cancer MGC-803 cell model. Our results demonstrated that quinazolin-4(3H)-one derivatives were suitable as leads for the development of novel USP7 inhibitors and especially for anti-gastric cancer drugs.

Self-catalyzed phototandem perfluoroalkylation/cyclization of unactivated alkenes: Synthesis of perfluoroalkyl-substituted quinazolinones

A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (Rf = CF3, C3F7, C4F9, C6F13, C8F17) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: Synthesis of quinazolinones containing the CF2R group

A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the Csp3-Br bond homolysis of alkyl bromides via a substrate (quinazolinones) induced energy transfer process. Additionally, the mild conditions, tolerance to a wide range of functional groups and operational simplicity make this protocol practical for the synthesis of fluorine-containing ring-fused quinazolinones. This journal is

Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones

A mild and efficient visible-light-induced radical difluoromethylation/cyclization of unactivated alkenes toward the synthesis of substituted quinazolinones with easily accessible difluoromethyltriphenylphosphonium bromide has been developed. The transformation has the advantages of wide functional group compatibility, a broad substrate scope, and operational simplicity. The benign protocol offers a facile access to pharmaceutically valuable difluoromethylated polycyclic quinazolinones.