75844-40-5

Usage

Uses

Used in Pharmaceutical Industry:
7-Methylquinazolin-4(1H)-one is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and properties make it a valuable building block in the development of new drugs.
Used in Agrochemical Industry:
7-Methylquinazolin-4(1H)-one is used as a chemical intermediate in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Antitumor Applications:
7-Methylquinazolin-4(1H)-one is studied for its potential use as an antitumor agent. Its ability to target and inhibit the growth of cancer cells makes it a promising candidate for further research and development in oncology.
Used in Antibacterial Applications:
7-Methylquinazolin-4(1H)-one has demonstrated antibacterial activity, making it a candidate for the development of new antibiotics to combat bacterial infections. Its potential use in this area is currently under investigation.

InChI:InChI=1/C9H8N2O/c1-6-2-3-7-8(4-6)10-5-11-9(7)12/h2-5H,1H3,(H,10,11,12)

Upstream product

• 64-18-6 formic acid 
• 39549-79-6 2-amino-4-methylbenzamide 
• 26830-96-6 5-methyl-2-cyanoaniline 
• 77287-34-4 formamide 
• 2305-36-4 4-methylanthranilic acid 
• 67-56-1 methanol 
• 1829-21-6 4-methyl-2-iodobenzoic acid 
• 6313-33-3 formamidine hydrochloride 
• 144-62-7 oxalic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 50424-81-2 4-methyl-2-nitro-benzoyl chloride 
• 122-51-0 orthoformic acid triethyl ester 
• 65078-05-9 4-methyl-2-nitrobenzamide 
• 27329-27-7 4-methyl-2-nitrobenzoic acid 

Downstream Products

• 90272-83-6 4-chloro-7-methylquinazoline 
• 1449737-58-9 5-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine 
• 943606-89-1 7-methyl-N⁴-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine 
• 1093101-62-2 4-(8-(3-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-20-9 4-(8-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-56-1 N₈-(3-(9H-purin-6-yl)pyridin-2-yl)-7-methyl-N₄-(3-(trifluoromethyl)phenyl)quinazolin-4,8-diamine 
• 1093100-61-8 N₈-(3-(9H-purin-6-yl)pyridin-2-yl)-N₄-(4-(difluoromethoxy)phenyl)-7-methylquinazoline-4,8-diamine 
• 1093100-60-7 N₈-(3-(9H-purin-6-yI)pyridin-2-yl)-N₄-(3-ethynylphenyl)-7-methylquinazoline-4,8-diamine 
• 1093100-21-0 4-(8-(3-(9H-purin-6-yI)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-19-6 4-(8-(3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-51-6 4-(8-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-62-9 N₈-(3-(9H-purin-6-yI)pyridin-2-yI)-N₄-(4-chIorophenyl)-7-methylquinazoline-4,8-diamine 
• 1093101-47-3 4-(6-bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrile 
• 1093101-48-4 4-(8-amino-7-methylquinazolin-4-ylamino)benzonitrile 

Relevant academic research and scientific papers

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.

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.

Design, Synthesis and Bioevaluation of Two Series of 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines

Two series of 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines were designed initially as potential acetylcholine esterase inhibitors. Biological evaluation demonstrated that N-(1-benzylpiperidin-4-yl)quinazolin-4-amines significantly inhibited AChE activity. Especially, two compounds of them were found to be the most potent with relative AChE inhibition percentages of 87 percent in comparison to donepezil. The docking studies with AChE showed similar interactions between donepezil and four derivatives. N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines also exhibited significant DPPH scavenging effects. The two series of compound also exerted moderate to good cytotoxicity against three human cancer cell lines, including SW620 (human colon cancer), PC-3 (prostate cancer), and NCI?H23 (lung cancer), with 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one being the most cytotoxic agent. 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one significantly induced early apoptosis and arrested the SW620 cells at G2/M phase. From this study, two compounds of N-(1-benzylpiperidin-4-yl)quinazolin-4-amines could serve as new leads for further design and AChE inhibitors, while 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one could serve as a new lead for the design and development of more potent anticancer agents.

3,4-DIHYDRO-4-OXOQUINAZOLINE-BASED ACETOHYDRAZIDES AND AN ANTICANCER COMPOSITION COMPRISING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to 3,4 - dihydro -4 -oxoquinazolinediazide and an anticancer composition comprising the same as an active ingredient. , It will be described below. 3,4 - Dihydro -4 - oxoquinazolin-based acetohydrazide according to the present invention activates procacaspase -3 to promote the conversion to caspase -3, and thus 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.