56071-04-6

Usage

Uses

Used in Pharmaceutical Industry:
4(3H)-Quinazolinone, 2-(3-Methoxyphenyl)is used as a pharmacological agent for its ability to act as an antagonist at the serotonin 5-HT2A receptor. This property makes it a candidate for the development of drugs targeting various neurological and psychiatric disorders associated with the serotonin system.
Used in Neuroprotective Applications:
In the field of neuroprotection, 4(3H)-Quinazolinone, 2-(3-Methoxyphenyl)is utilized for its potential to protect neurons from damage or degeneration. Its neuroprotective effects are of interest for the development of treatments for neurodegenerative diseases such as Alzheimer's, Parkinson's, and multiple sclerosis.
Used in Anti-Inflammatory Applications:
4(3H)-Quinazolinone, 2-(3-Methoxyphenyl)is also used as an anti-inflammatory agent. Its potential to reduce inflammation is being explored for the development of treatments for various inflammatory conditions, including arthritis, asthma, and inflammatory bowel diseases.
Used in Drug Discovery Research:
In the realm of drug discovery, 4(3H)-Quinazolinone, 2-(3-Methoxyphenyl)serves as a valuable research tool. Its unique structure and pharmacological properties make it an interesting target for the development of new drugs with novel mechanisms of action, potentially leading to more effective treatments for a variety of diseases.

Upstream product

• 28144-70-9 anthranilic acid amide 
• 591-31-1 3-methoxy-benzaldehyde 
• 6971-51-3 3-methoxybenzyl alcohol 
• 610-15-1 2-nitrobenzamide 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 1798-09-0 m-methoxyphenylacetic acid 
• 64559-06-4 3-methoxythiobenzamide 
• 13939-06-5 molybdenum hexacarbonyl 
• 1527-89-5 3-methoxybenzonitrile 
• 1885-29-6 anthranilic acid nitrile 
• 766-85-8 3-methoxy-1-iodobenzene 
• 144-62-7 oxalic acid 
• 7290-99-5 N,N-dimethyl-m-methoxybenzamide 
• 6192-52-5 p-toluenesulfonic acid monohydrate 

Downstream Products

• 1448068-54-9 C₁₆H₁₃N₅O 
• 1448069-14-4 2-(3-methoxyphenyl)-3,4-dihydroquinazolin-4-thione 
• 1217862-32-2 C₁₅H₁₄N₄O 
• 329024-94-4 4-ethoxy-2-(3-methoxyphenyl)quinazoline 
• 911417-67-9 tert-butyl 5-(2-(3-(2-(2-(dimethylamino)-ethylamino)-2-oxoethoxy)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate 

Relevant academic research and scientific papers

A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones

Magnetic manganese dioxide nanoparticles (MnO2-Fe3O4) were coated on sugarcane bagasse as a sugar industrial waste and bio-support (MnO2-Fe3O4@bagasse) via an in situ reduction strategy, in which potassium permanganate was used as the precursor of MnO2 and sugarcane bagasse as a bio-support and reducing agent of KMnO4. The synthesized bio-based catalyst was characterized by X-ray diffraction, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, Brunauer–Emmett–Teller surface area analysis, and vibrating sample magnetometer analysis. The catalyst was successfully utilized in the selective aerobic oxidation of primary and secondary benzylic alcohols to their corresponding carbonyl compounds and one-pot tandem oxidative synthesis of 2-(substituted)quinazoline-4(3H)-ones from the o-aminobenzamide and aromatic alcohols in the absence of oxidizing reagent or initiator. Graphical abstract: [Figure not available: see fulltext.]

Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO

A novel approach for the synthesis of 2-arylquinazolin-4(3H)-ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO-mediated intramolecular oxidative cross-coupling of 2-(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram-scale synthesis. A proposed reaction pathway based on some control experiments was also provided.

Iron catalyzed metal-ligand cooperative approaches towards sustainable synthesis of quinolines and quinazolin-4(3H)-ones

Herein we report simple, efficient, and economically affordable metal-ligand cooperative strategies for synthesizing quinolines and quinazolin-4(3H)-ones via dehydrogenative functionalization of alcohols. Various polysubstituted quinolines and quinazolin-4(3H)-ones were prepared in good yields via dehydrogenative coupling of readily available alcohols with ketones and 2-aminobenzamides, respectively under air using a well-defined Fe(II)-catalyst, ([FeL1Cl2] (1)) bearing a redox-active azo-aromatic pincer 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline) (L1). Control experiments and mechanistic investigation disclose that the one-electron reduced mono-anionic species [1]? bearing an iron-stabilized azo-anion radical ligand catalyzes these reactions. Both iron and the redox-active arylazo ligand participate synergistically during the different steps of these catalytic reactions.

Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution

The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.

Electro-oxidative cyclization: Access to quinazolinones: Via K2S2O8without transition metal catalyst and base

A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure, leading to the formation of nitrogen heterocycles via direct oxidative cyclization at room temperature in a one-pot procedure under constant current. Owing to the use of continuous-flow electrochemical setups, this green, mild and practical electrosynthesis features high efficiency and excellent functional group tolerance and is easy to scale up.

Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach

Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.

Design, synthesis, characterization, enzymatic inhibition evaluations, and docking study of novel quinazolinone derivatives

In this study, novel quinazolinone derivatives 7a-n were synthesized and evaluated against metabolic enzymes including α-glycosidase, acetylcholinesterase, butyrylcholinesterase, human carbonic anhydrase I, and II. These compounds exhibited high inhibitory activities in comparison to used standard inhibitors with Ki values in the range of 19.28–135.88 nM for α-glycosidase (Ki value for standard inhibitor = 187.71 nM), 0.68–23.01 nM for acetylcholinesterase (Ki value for standard inhibitor = 53.31 nM), 1.01–29.56 nM for butyrylcholinesterase (Ki value for standard inhibitor = 58.16 nM), 10.25–126.05 nM for human carbonic anhydrase I (Ki value for standard inhibitor = 248.18 nM), and 13.46–178.35 nM for human carbonic anhydrase II (Ki value for standard inhibitor = 323.72). Furthermore, the most potent compounds against each enzyme were selected in order to evaluate interaction modes of these compounds in the active site of the target enzyme. Cytotoxicity assay of the title compounds 7a-n against cancer cell lines MCF-7 and LNCaP demonstrated that these compounds do not show significant cytotoxic effects.

Synthesis of Difluoromethyl-Substituted Quinazolines through Selective Difluoromethylation

A highly selective difluoromethylation of quinazolines has been achieved by using commercially available ethyl bromodifluoroacetate as difluorocarbene precursor, providing the corresponding difluoromethyl substituted quinazoline derivatives with up to 83% yield.

Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation

Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.