16064-14-5

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-4-hydroxyquinazoline is utilized as a synthetic intermediate for the production of various pharmaceuticals. Its ability to inhibit bacterial growth makes it a promising candidate in the development of new antibiotics, addressing the growing need for effective treatments against drug-resistant bacteria.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Chloro-4-hydroxyquinazoline serves as a key building block in the synthesis of bioactive compounds, including pesticides and herbicides. Its incorporation into these products can enhance their efficacy in controlling pests and weeds, thereby improving crop yields and food security.
Used in Organic Synthesis:
6-Chloro-4-hydroxyquinazoline is employed as a versatile building block in organic synthesis for the preparation of a wide range of bioactive compounds. Its unique structural features allow for the creation of diverse chemical entities with potential applications in various fields, such as medicine, agriculture, and materials science.
Handling and Storage:
6-Chloro-4-hydroxyquinazoline is typically handled and stored in accordance with standard laboratory procedures for organic chemicals. Proper safety measures, including the use of personal protective equipment and adherence to hazard communication guidelines, are essential to ensure the safe handling and storage of 6-Chloro-4-hydroxyquinazoline.

InChI:InChI=1/C8H5ClN2O/c9-5-1-2-7-6(3-5)8(12)11-4-10-7/h1-4H,(H,10,11,12)

Upstream product

• 491-36-1 4-Hydroxyquinazoline 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 77287-34-4 formamide 
• 635-21-2 5-chloroanthranilic acid 
• 4743-17-3 5-Chloroisatoic anhydride 
• 6313-33-3 formamidine hydrochloride 
• 7782-50-5 chlorine 
• 7705-08-0 iron(III) chloride 
• 64-19-7 acetic acid 
• 5202-85-7 2-Amino-5-chlorobenzamide 
• 149-73-5 trimethyl orthoformate 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 118-92-3 anthranilic acid 

Downstream Products

• 7253-22-7 4,6-dichloroquinazoline 
• 7505-75-1 4-ethoxy-6-chloro-quinazoline 
• 1087750-38-6 C₁₄H₈ClFN₂O 
• 24585-93-1 3-benzyl-6-chloroquinazolin-4(3H)-one 

Relevant academic research and scientific papers

Substituted isoquinolines and quinazolines as potential antiinflammatory agents. Synthesis and biological evaluation of inhibitors of tumor necrosis factor α

A series of isoquinolin-1-ones and quinazolin-4-ones and related derivatives were prepared and evaluated for their ability to inhibit tumor necrosis factor α (TNFα) production in human peripheral blood monocytes stimulated with bacterial lipopolysaccharide (LPS). In an effort to optimize the TNFα inhibitory activity, a homologous series of N-alkanoic acid esters was prepared. Several electrophilic and nucleophilic substitutions were also carried out. Alkanoic acid esters of four carbons were found to be optimum for activity in both the isoquinoline and quinazoline series. Ring substituents such as fluoro, bromo, nitro, acetyl, and aminomethyl on the isoquinoline ring resulted in a significant loss of activity. Likewise, similar groups on the quinazoline ring also reduced inhibitory activity. However, the 6- and 7-aminoquinazoline derivatives, 75 and 76, were potent inhibitors, with IC50 values in the TNFα in vitro assay of approximately 5 μM for each. An in vivo mouse model of pulmonary inflammation was then used to evaluate promising candidate compounds identified in the primary in vitro assay. Compound 75 was selected for further study in this inhalation model, and was found to reduce the level of TNFα in brochoalveolar lavage fluid of LPS-treated mice by about 50% that of control mice. Thus, compounds such as 75, which can effectively inhibit proinflammatory cytokines such as TNFα in clinically relevant animal models of inflammation and fibrosis, may have potential as new antiinflammatory agents. Finally, a quinazoline derivative suitable to serve as a photoaffinity radiolabeled compound was prepared to help identify the putative cellular target(s) for these TNFα inhibitors.

Novel quinazolinone inhibitors of the Pseudomonas aeruginosa quorum sensing transcriptional regulator PqsR

Rising numbers of cases of multidrug- and extensively drug-resistant Pseudomonas aeruginosa over recent years have created an urgent need for novel therapeutic approaches to cure potentially fatal infections. One such approach is virulence attenuation where anti-virulence compounds, designed to reduce pathogenicity without affording bactericidal effects, are employed to treat infections. P. aeruginosa uses the pqs quorum sensing (QS) system, to coordinate the expression of a large number of virulence determinants as well as bacterial-host interactions and hence represents an excellent anti-virulence target. We report the synthesis and identification of a new series of thiazole-containing quinazolinones capable of inhibiting PqsR, the transcriptional regulator of the pqs QS system. The compounds demonstrated high potency (IC50 pqsA-lux-based bioreporter for the P. aeruginosa PAO1-L and PA14 strains. Structural evaluation defined the binding modes of four analogues in the ligand-binding domain of PqsR through X-ray crystallography. Further work showed the ability of 6-chloro-3((2-pentylthiazol-4-yl)methyl)quinazolin-4(3H)-one (18) and 6-chloro-3((2-hexylthiazol-4-yl)methyl)quinazolin-4(3H)-one (19) to attenuate production of the PqsR-regulated virulence factor pyocyanin. Compounds 18 and 19 showed a low cytotoxic profile in the A549 human epithelial lung cell line making them suitable candidates for further pre-clinical evaluation.

Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation

Cytotoxic and antimicrobial agents structurally based on quinazolinone, benzofuran and imidazole pharmacophores, have been designed and synthesized. Spectral (IR, 1H-NMR) and elemental analysis data established the structures of these novel 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride hybrid derivatives. All the synthesized compounds were evaluated for in?vitro cytotoxicity and antimicrobial activities. Cytotoxic evaluation using MTT assay revealed that compounds 12c, 12g and 12i exhibited significant cytotoxicity with IC50 values 1, 1, and 0.57?μm on this cell line, respectively. Biological activity of the synthesized compounds as antibacterial agent were also evaluated against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-positive (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungi (Candida albicans) strains. All compounds 12a?–?12i showed slightly higher activity against Gram-positive bacteria than the Gram-negative one. Among the nine new compounds screened, 3-[1-(5-bromo-1-benzofuran-2-yl)-2-(6-chloro-4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride (12e) has pronounced higher antimicrobial activity against all tested strains. These results demonstrated potential importance of molecular hybridization in the development of new lead molecules with major cytotoxicity and antimicrobial activity.

A decarboxylative traceless linker approach for the solid phase synthesis of quinazolines

A decarboxylative traceless linker strategy for the cleavage of resin- bound quinazolines has been developed using hydroxymethylpolystyrene (HMPS) resin derivatised as the ethyl oxalate. Methods for the solid phase synthesis of the linker, quinazoline formation, functionalisation and cleavage are described.

Synthesis and antifungal bioactivities of 3-alkylquinazolin- 4-one derivatives

A simple, efficient, and general method has been developed for the synthesis of various 3-alkylquinazolin-4-one derivatives from quinazolin-4-one treated with alkyl bromides under phase transfer catalysis condition. The structures of the compounds were characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. Title compound 6-bromo-3-propylquinazolin-4-one (3h) was found to possess good antifungal activity.

A New Synthesis of Aryl Substituted Quinazolin-4(1H)-ones

Treatment of a variety of substituted 2-aminobenzonitriles with formic acid under strong acid catalysis provides the corresponding quinazolin-4(1H)-ones in good yield. A potential reaction pathway is described.

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.

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.

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.