19181-53-4

Usage

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-6-METHYLQUINAZOLINE is used as a building block for the synthesis of pharmaceuticals due to its potential biological activities and its role in various biological pathways and physiological processes.
Used in Drug Development:
4-HYDROXY-6-METHYLQUINAZOLINE is used in drug development for its potential anti-cancer and anti-inflammatory properties, making it a promising candidate for the development of new therapeutic agents.
Used in Research:
4-HYDROXY-6-METHYLQUINAZOLINE is used in research to study its role in various biological pathways and physiological processes, contributing to the understanding of its potential applications in medicine and pharmacology.

InChI:InChI=1/C11H15NO2/c1-3-12(4-2)11(14)9-7-5-6-8-10(9)13/h5-8,13H,3-4H2,1-2H3

Upstream product

• 58421-79-7 4-chloro-6-methylquinazoline 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 77287-34-4 formamide 
• 64392-62-7 formamidinium acetate 
• 40545-33-3 2-amino-5-methylbenzamide 
• 149-73-5 trimethyl orthoformate 
• 5925-93-9 2-amino-5-methylbenzonitrile 
• 64407-07-4 3-(chloromethyl)benzonitrile 
• 3113-72-2 5-methyl-2-nitrobenzoic acid 
• 620-22-4 3-Methylbenzonitrile 
• 99-04-7 m-Toluic acid 
• 67-56-1 methanol 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 
• 6313-33-3 formamidine hydrochloride 

Downstream Products

• 58421-79-7 4-chloro-6-methylquinazoline 
• 92554-57-9 6-methyl-N-phenylquinazolin-4-amine 
• 303120-13-0 N-benzyl-6-methylquinazolin-4-amine 
• 1442476-74-5 (1E,4E)-1-(4-fluorophenyl)-5-(4-(6-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 
• 1442476-77-8 (1E,4E)-1-(4-chlorophenyl)-5-(4-(6-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 

Relevant academic research and scientific papers

Design and synthesis of novel artemisinin derivatives with potent activities against colorectal cancer in vitro and in vivo

A series of novel derivatives of artemisinin-4-(arylamino)quinazoline have been designed and synthesized, and most of them showing potent in vitro cytotoxic activity against HCT116 and WM-266-4 cell lines. Compound 32 was the most active derivative against HCT116 cell line with an IC50 of 110 nM, and significantly improved the antitumor activity of the parent compounds dihydroartemisinin (DHA) (IC50 = 2.85 μM) and Gefitinib (IC50 = 19.82 μM). In vivo HCT116 xenografts assay showed that compound 32 exhibited potent antitumor activity with obvious tumor growth delay and tumor shrunken after 18 days treatment on xenografted mice, and especially without loss of body weight. Our results indicate that compounds 32 may represent a safe, novel structural lead for developing new chemotherapy of colorectal cancer.

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.

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

Synthesis, Anti-Tomato Spotted Wilt Virus Activities, and Interaction Mechanisms of Novel Dithioacetal Derivatives Containing a 4(3 H)-Quinazolinone Pyrimidine Ring

A series of unreported novel dithioacetal derivatives containing a 4(3H)-quinazolinone pyrimidine ring were synthesized, and their antiviral activities were evaluated against tomato spotted wilt virus (TSWV). A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis was established, and compound D32 was designed and synthesized according to the analysis results of the CoMFA and CoMSIA models. The bioassay results showed that compound D32 exhibited excellent inactivation activity against TSWV, with EC50 values of 144 μg/mL, which was better than those of ningnanmycin (149 μg/mL) and the lead compound xiangcaoliusuobingmi (525 μg/mL). The binding ability of compound D32 to TSWV CP was tested by microscale thermophoresis (MST), and the binding constant value was 4.4 μM, which was better than those of ningnanmycin (6.2 μM) and xiangcaoliusuobingmi (59.1 μM). Therefore, this study indicates that novel dithioacetal derivatives containing a 4(3H)-quinazolinone pyrimidine ring may be applied as new antiviral agents.

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.