1788-93-8

Usage

Uses

Used in Pharmaceutical Industry:
Pirenzepine is utilized as a therapeutic agent for the treatment of peptic ulcers due to its ability to selectively block muscarinic receptors, thereby reducing gastric acid secretion and promoting healing of ulcers.
Used in Neurological Applications:
As a cognitive enhancer, pirenzepine is employed to potentially improve cognitive functions by modulating the activity of muscarinic receptors in the brain, which are implicated in various cognitive processes.
Used in Respiratory Conditions Treatment:
Pirenzepine is explored for its potential use in treating chronic obstructive pulmonary disease and other respiratory conditions, leveraging its antagonistic effect on muscarinic receptors to alleviate symptoms and improve lung function.
Used in Drug Development Research:
Pirenzepine's unique chemical structure and properties make it a valuable compound for further research and development, particularly in the area of therapeutics targeting muscarinic receptors for a range of medical applications.

InChI:InChI=1/C15H11ClN2O.ClH/c1-10-17-14-5-3-2-4-13(14)15(19)18(10)12-8-6-11(16)7-9-12;/h2-9H,1H3;1H

Upstream product

• 106-47-8 4-chloro-aniline 
• 108-88-3 toluene 
• 89-52-1 o-acetylamino-benzoic acid 
• 7719-12-2 phosphorus trichloride 
• 118-48-9 isatoic anhydride 
• 78-39-7 Triethyl orthoacetate 
• 118-92-3 anthranilic acid 
• 75-16-1 methylmagnesium bromide 
• 622403-43-4 2-(4-Chloro-phenyliminomethyleneamino)-benzoic acid ethyl ester 
• 179039-70-4 ethyl 2-(triphenylphosphoranylidene-amino)benzoate 
• 90408-05-2 o-azidobenzoic acid ethyl ester 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 134-20-3 2-carbomethoxyaniline 
• 75-05-8 acetonitrile 

Downstream Products

• 128457-98-7 3-(4-Chloro-phenyl)-2-((E)-3-oxo-3-p-tolyl-propenyl)-3H-quinazolin-4-one 
• 128457-94-3 3-(4-Chloro-phenyl)-2-((E)-3-oxo-3-phenyl-propenyl)-3H-quinazolin-4-one 
• 80806-72-0 3-(4-Chloro-phenyl)-2-[(E)-2-(4-hydroxy-3-nitro-phenyl)-vinyl]-3H-quinazolin-4-one 
• 81541-41-5 3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-2-carbaldehyde 
• 61554-51-6 2-Bromomethyl-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 596807-51-1 2-(3-chloro-2-oxo-propyl)-3-(4-chlorophenyl)-3H-quinazolin-4-one 
• 80884-23-7 3-(4-Chloro-phenyl)-2-[(2,4-dimethyl-benzylamino)-methyl]-3H-quinazolin-4-one 
• 80884-16-8 3-(4-Chloro-phenyl)-2-[(2-p-tolyl-ethylamino)-methyl]-3H-quinazolin-4-one 
• 80884-18-0 3-(4-Chloro-phenyl)-2-{[2-(4-chloro-phenyl)-ethylamino]-methyl}-3H-quinazolin-4-one 
• 80884-21-5 3-(4-Chloro-phenyl)-2-[(2,4-dichloro-benzylamino)-methyl]-3H-quinazolin-4-one 

Relevant academic research and scientific papers

Microwae-assisted one-pot three component synthesis of some new 4(3H)-quinazolinone derivatives

Efficient microwave-assisted synthesis of 4(3H)-quinazolinones by the one-pot three-component condensation of isatoic anhydride, primary amines and orthoesters in the presence of catalytic amounts of p-toluenesulfonic acid in high yields is reported.

A novel superparamagnetic powerful guanidine-functionalized γ-Fe2O3based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4(3H)-one derivatives in Green media

The novel organic-inorganic nanohybrid superparamagnetic (γ-Fe2O3@CPTMS-guanidine@SO3H) nanocatalyst modified with sulfonic acid represents an efficient and green catalyst for the one-pot synthesis of quinazolin-4(3H)-one derivativesviathree-component condensation reaction between anthranilic acid, acetic anhydride and different amines under microwave irradiation and solvent-free conditions (4a-q). XRD, FT-IR, FE-SEM, TGA, VSM and EDX were used to characterize this new magnetic organocatalyst. Outstanding performance, short response time (15-30 min), simple operation, easy work-up procedure, and avoidance of toxic catalysts can be regarded as its significant advantages. Moreover, it can be easily separated from the reaction solution through magnetic decantation using an external magnet, and recycled at least six times without notable reduction in its activity.

Metal-free C-H methylation and acetylation of heteroarenes with PEG-400

The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.

Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation

One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone.

Synthesis, Characterization, and Biological Evaluation of Novel 3-(4-Chlorophenyl)-2-(substituted)quinazolin-4(3H)-one Derivatives as Multi-target Anti-inflammatory Agents

A novel class of 3-(4-chlorophenyl)-2-(substituted)quinazolin-4(3H)-one derivatives were synthesized, and the structure of synthesized compounds was characterized by IR, 1H NMR, and mass spectroscopy. The newly synthesized compounds (4a–g and 6a–g) were tested for their in vitro cyclooxygenase (COX) inhibition activity. The compounds have inhibitory profile against both COX-1 and COX-2, and some of the compounds are found to be selective against COX-2. The compound 6g showed distinct inhibitory activity on COXs. The synthesized compounds were evaluated for their potential anti-inflammatory activity as inhibitors of the proinflammatory cytokines IL-6. Compounds 4d–g showed the highest level of inhibition among all the tested compounds. Thus, our data suggested that these compounds may represent a new class of potent anti-inflammatory agents.

Screening of natural deep eutectic solvents for green synthesis of 2-methyl-3-substituted quinazolinones and microwave-assisted synthesis of 3-aryl quinazolinones in ethanol

In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1: 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.

A facile synthesis of quinazolinone derivatives through Vilsmeier intermediate

The reaction of ethyl 2-aminobenzoate with different substituted amide compounds led to cyclization through Vilsmeier intermediate in dry dichloromethane and ambient temperature, affording the 4(3H)-quinazolinone derivatives with higher yields. The struct

Expeditious synthesis and spectroscopic characterization of 2-methyl-3-substituted-quinazolin-4(3H)-one derivatives

Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.

Approach to the Synthesis of 2,3-Disubstituted-3H-quinazolin-4-ones Mediated by Ph3P-I2

Readily available N-substituted amides or their requisite carboxylic acids or acid chlorides have been used to construct 2,3-disubstituted-3H-quinazolin-4-ones in a one-pot procedure. Key transformation in this convergent approach involves Ph3P-I2-mediated formation of amidine upon condensation of an amide or the intermediate amide with methyl anthranilate. Cyclization of the amidine-tethered anthranilate then affords 2,3-disubstituted-3H-quinazolin-4-ones in good to excellent yields under mild conditions.

A quinazoline compound and its synthesis method

The invention discloses a synthetic method of a quinazolinone compound. The method can be used for preparing the quinazolinone compound by carrying out reaction at a proper temperature and time by taking a 2-aminobenzamide derivative and a 1, 3-diketone compound as raw materials, taking chiral Bronsted acid or Lewis acid as a catalyst and water and biodegradable ethyl lactate and polyethylene glycol as a mixed solvent. The synthetic method of the quinazolinone compound provided by the invention is mild in reaction condition, low in cost, environment-friendly, high in yield and suitable for industrial production.