1788-93-8

Basic information

• Product Name: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon
• Synonyms: 2-methyl-3-(4’-chlorphenyl)chinazolon-(4);2-methyl-3-(4-chlorophenyl)-4(3h)-quinazolinone;3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon;2-methyl-3-(4-chlorophenyl)quinazolin-4-one
• CAS NO: 1788-93-8
• Molecular Formula: C₁₅H₁₁ClN₂O
• Molecular Weight: 270.71364
• Mol File: 1788-93-8.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 439°Cat760mmHg
• Flash Point: 219.3°C
• Appearance: /
• Density: 1.2576 (rough estimate)
• Vapor Pressure: 6.6E-08mmHg at 25°C
• Refractive Index: 1.6330 (estimate)
• CAS DataBase Reference: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon(1788-93-8)
• EPA Substance Registry System: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon(1788-93-8)

Safety Data

• Hazardous Substances Data: 1788-93-8(Hazardous Substances Data)

Usage

Description

3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon, also known as pirenzepine, is a chemical compound belonging to the quinazolinone class. It is characterized by its potential use as an antagonist of the muscarinic acetylcholine receptors, particularly showing high affinity for the M1 subtype. This feature positions pirenzepine as a promising candidate for therapeutic applications in various medical conditions.

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

• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 106-47-8 4-chloro-aniline 
• 20265-96-7 p-chloroaniline hydrochloride 
• 25116-00-1 2-acetamidobenzonitrile 
• 118-92-3 anthranilic acid 
• 24122-31-4 3-(4-chlorophenyl)quinazolin-4(3H)-one 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 87-25-2 2-ethoxycarbonylaniline 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 134-20-3 2-carbomethoxyaniline 
• 75-05-8 acetonitrile 
• 108-24-7 acetic anhydride 
• 4943-86-6 2-amino-N-(4-chlorophenyl)benzamide 
• 123-54-6 acetylacetone 

Downstream Products

• 61554-51-6 2-Bromomethyl-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 81541-41-5 3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-2-carbaldehyde 
• 80806-72-0 3-(4-Chloro-phenyl)-2-[(E)-2-(4-hydroxy-3-nitro-phenyl)-vinyl]-3H-quinazolin-4-one 
• 128457-94-3 3-(4-Chloro-phenyl)-2-((E)-3-oxo-3-phenyl-propenyl)-3H-quinazolin-4-one 
• 128457-98-7 3-(4-Chloro-phenyl)-2-((E)-3-oxo-3-p-tolyl-propenyl)-3H-quinazolin-4-one 
• 37856-32-9 3-(4-chlorophenyl)-2-styrylquinazolin-4(3H)-one 
• 115781-69-6 3-p-chlorophenyl-2-styryl-3,4-dihydro-4-quinazolone 
• 131532-94-0 3-(4-Chloro-phenyl)-2-{[3-(4-chloro-phenyl)-4-phenyl-3H-thiazol-(2Z)-ylidene]-hydrazonomethyl}-3H-quinazolin-4-one 
• 131532-95-1 3-(4-Chloro-phenyl)-2-{[4-phenyl-3-p-tolyl-3H-thiazol-(2Z)-ylidene]-hydrazonomethyl}-3H-quinazolin-4-one 
• 128458-16-2 2-[2-(4-Bromo-phenyl)-5-p-tolyl-2H-pyrazol-3-yl]-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 131533-03-4 3-(4-Chloro-phenyl)-2-{[3-(4-chloro-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-hydrazonomethyl}-3H-quinazolin-4-one 
• 128458-08-2 3-(4-Chloro-phenyl)-2-(2,5-di-p-tolyl-2H-pyrazol-3-yl)-3H-quinazolin-4-one 

Relevant articles and documents

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.

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.

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.