22312-80-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(CHLOROMETHYL)-3-(4-METHYLPHENYL)QUINAZOLIN-4(3H)-ONE is used as a potential therapeutic agent for its anti-inflammatory and antitumor activities. Its pharmacological properties make it a candidate for the development of new drugs to treat various diseases, including cancer.
Used in Drug Discovery and Development:
2-(CHLOROMETHYL)-3-(4-METHYLPHENYL)QUINAZOLIN-4(3H)-ONE serves as a promising chemical entity in drug discovery and development. Its unique structure and potential pharmacological properties allow researchers to explore its use in creating new drugs with improved efficacy and safety profiles.

Upstream product

• 106-49-0 p-toluidine 
• 118-92-3 anthranilic acid 
• 14422-49-2 2-chloroacetamidobenzoic acid 
• 22312-66-9 2-(2-chloro-acetylamino)-N-p-tolyl-benzamide 

Downstream Products

• 1189553-15-8 C₃₀H₃₂N₂O₁₀S 
• 1189553-21-6 C₂₇H₂₈N₂O₈S 
• 952612-86-1 N-(5-(4-oxo-3-p-tolyl-3,4-dihydroquinazolin-2-yl)-4-phenylthiazol-2-yl)benzamide 
• 1413930-43-4 1-[(4-oxo-3-p-tolyl-3,4-dihydroquinazolin-2-yl)methyl]-1,4-dihydro-4-oxo-3-pyridinesulfonamide 

Relevant academic research and scientific papers

Substituted 4-phenylthiazoles: Development of potent and selective A1, A3 and dual A1/A3 adenosine receptor antagonists

Adenosine acts as a powerful signaling molecule via four distinct G protein-coupled receptors, designated A1, A2A, A2B and A3 adenosine receptors (ARs). A2A and A2B ARs are Gs-coupled, while A1 and A3 ARs inhibit cAMP production via Gi proteins. Antagonists for A1 and A3 ARs may be useful for the treatment of (neuro)inflammatory diseases including acute kidney injury and kidney failure, pulmonary diseases, and Alzheimer's disease. In the present study, we optimized the versatile 2-amino-4-phenylthiazole scaffold by introducing substituents at N2 and C5 to obtain A1 and A3 AR antagonists including dual-target compounds. Selective A1 antagonists with (sub)nanomolar potency were produced, e.g. 11 and 13. These compounds showed species differences being significantly more potent at the rat as compared to the human A1 AR, and were characterized as inverse agonists. Several potent and selective A3 AR antagonists, e.g. 7, 8, 17 and 22 (Ki values of 5–9 nM at the human A3 AR) were prepared, which were much less potent at the rat orthologue. Moreover, dual A1/A3 antagonists (10, 18) were developed showing Ki values between 8 and 42 nM. Docking and molecule dynamic simulation studies using the crystal structure of the A1 AR and a homology model of the A3 AR were performed to rationalize the observed structure-activity relationships.

Novel 2,4- thiazolidinediones: Synthesis, in?vitro cytotoxic activity, and mechanistic investigation

Two thiazolidinedione scaffolds different in the position of the thiazolidinedione ring in the molecule were tested for in?vitro cytotoxic activity in a panel of human cancer cell lines namely, prostate cancer cells PC-3, breast carcinoma cells MDA-MB-231

Quinazolinone-based rhodanine-3-acetic acids as potent aldose reductase inhibitors: Synthesis, functional evaluation and molecular modeling study

A series of quinazolinone-based rhodanine-3-acetic acids was synthesized and tested for in vitro aldose reductase inhibitory activity. All the target compounds displayed nanomolar activity against the target enzyme. Compounds 3a, 3b, and 3e exhibited almo

Design, synthesis and evaluation of novel 2-thiophen-5-yl-3H-quinazolin-4-one analogues as inhibitors of transcription factors NF-k{cyrillic}B and AP-1 mediated transcriptional activation: Their possible utilization as anti-inflammatory and anti-cancer ag

In an attempt to discover novel inhibitors of NF-κB and AP-1 mediated transcriptional activation utilizing the concept of chemical lead based medicinal chemistry and bioisosterism a series of 2-(2,3-disubstituted-thiophen-5-yl)-3H-quinazolin-4-one analogs

Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents

A series of 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives were designed and synthesized. Synthesized molecules were further evaluated for their inhibitory activity towards transcription factors NF-κB and AP-1 mediated transcr

Synthesis of novel thioglycoside derivatives containing quinazolinone

Aseries of novel thioglycoside derivatives containing 4(3H)-quinazolinone was designed and synthesized from 2-chloromethyl-quinazolin-4(3H)-ones and 1-thioglycose. Several 2-chloromethyl-quinazolin-4(3H)-ones were synthesized on refluxing with 2-(chloroacetylamino)-benzoic acid and arylamines in acetonitrile. All of the novel compounds were characterized by IR, 1H NMR spectra and elemental analysis. The structures of compounds 7b, 8b and 8c have been determined by X-ray diffraction analysis.

THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS

Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.

Synthesis and in vitro antifungal activity of some N,N-disubstituted dithiocarbamic acid esters derived from 2-methylquinazolinones

A series of 2-[(N,N-disubstituted thiocarbamoylthio)methyl]quinazolinones 9a-g; 10a; 10d; 11a-d and 12a were synthesized and evaluated for potential antifungal activity against a variety of fungal species. The synthesis of the target compounds was achieved by reaction of the potassium salts of disubstituted dithiocarbamic acids 8a-g and the respective 2-bromomethyl-4(3H)-quinazolinone 4 or 3-aryl-2- chloromethyl-4(3H)-quinazolinones 5-7. The dithiocarbamic acid derivatives were synthesized in a one step reaction from the appropriate amine, alcoholic potassium hydroxide solution and carbon disulfide. TLC and elemental analyses ascertained the purity of the synthesized compounds and their structures were confirmed by IR and 1H-NMR spectroscopy, 2-Methyl-4(3H)-quinazolinone 2, the precursor of the 2-bromomethyl intermediate 4, was selected as representative example for detailed spectroscopic investigations, including 300 MHz 1H- and 13CNMR in addition to HH COSY; APT and 1H13C HETCOR spectra, with the aim of establishing correct assignment of the spectral data of related compounds. The synthesized disubstituted dithiocarbamates 9a-g; 10a,d; 11a-d and 12a as well as tolnaftate and clotrimazole, as reference drugs, were tested in vitro at 2 and 5% concentrations against 23 pathogenic fungi. The study revealed that compound 9a exhibited broad spectrum inhibitory activity that is superior or comparable to that of the reference drugs against the tested fungal isolates. Selective fungistatic activity against Candida species was elicited by compound 9e and against Microsporum species as well as Trichophyton mentagrophytes was also observed for compound 9g. As a general pattern it might be postulated that some of the synthesized dithiocarbamate derivatives showed broad spectrum antifungal activity as compared with tolnaftate, the clinically used thiocarbamate compound, and also exhibited comparable activity to clotrimazole against Candida species and F. Solani.

Synthesis and fungicidal activity of 3-aryl-2-(4'-aryl thiazol-2'-ylaminomethyl)quinazol-4(3H)-ones

A series of 3-aryl-2-(4'-aryl thiazol-2'-ylaminomethyl)quinazol-4(3H)-ones 3a-p have been prepared by condensing 3-aryl-2-chloromethylquinazol-4(3H)-ones with 2-amino-4-substituted phenylthiazoles. Another group of 3-aryl-6,8-dibromo-2-(4'-arylthiazol-2'-