1028-38-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is used as a potential candidate for the development of novel drugs due to its unique chemical structure and the possibility of exhibiting biological activity. Its quinazolinone core and chlorine substituent may contribute to its potential therapeutic effects, making it a valuable compound for further research and development in the pharmaceutical sector.
Used in Drug Discovery and Development:
In the field of drug discovery and development, 3-(3-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is utilized as a starting point for the synthesis of new compounds with potential therapeutic applications. Its unique structure may allow for the design of drugs targeting specific biological pathways or receptors, offering new treatment options for various diseases and conditions.
Used in Medicinal Chemistry Research:
3-(3-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE serves as a valuable compound in medicinal chemistry research, where scientists investigate its chemical properties, reactivity, and potential interactions with biological targets. Understanding these aspects can provide insights into its potential use as a therapeutic agent and guide the development of related compounds with improved pharmacological profiles.
Note: Since the provided materials do not specify the exact applications or industries for 3-(3-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE, the uses listed above are based on the general potential of quinazolinone derivatives in the pharmaceutical and chemical research fields. Further research and development would be necessary to determine the specific applications and industries where 3-(3-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE could be utilized.

InChI:InChI=1/C14H9ClN2OS/c15-9-4-3-5-10(8-9)17-13(18)11-6-1-2-7-12(11)16-14(17)19/h1-8H,(H,16,19)

Upstream product

• 75-15-0 carbon disulfide 
• 118-48-9 isatoic anhydride 
• 108-42-9 3-chloro-aniline 
• 53662-48-9 m-chlorophenyldithiocarbamic acid triethylamine salt 
• 118-92-3 anthranilic acid 
• 2392-68-9 3-chlorophenyl-isothiocyanate 
• 877-81-6 (3-Chloro-phenyl)-dithiocarbamic acid methyl ester 
• 4968-46-1 N-(3-chlorophenyl)cyanothioformanilide 

Downstream Products

• 67811-53-4 4-(3-chlorophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 66679-73-0 2-hydrazino-3-(3-chlorophenyl)quinazoline-4(3H)-one 
• 1146625-09-3 C₂₂H₁₅ClN₂O₃S 
• 1146625-08-2 C₁₉H₁₇ClN₂O₃S 
• 1146625-10-6 C₂₀H₁₉ClN₂O₃S 
• 1146625-07-1 C₂₀H₁₉ClN₂O₃S 
• 193826-39-0 [3-(3-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylsulfanyl]-acetic acid hydrazide 
• 193826-31-2 [3-(3-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylsulfanyl]-acetic acid methyl ester 
• 1012124-64-9 2-[3-(3-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylsulfanyl]-propionic acid methyl ester 
• 105362-96-7 3-Amino-2-(3-chloro-phenylamino)-3H-quinazolin-4-one 
• 108534-39-0 3-(3-Chloro-phenyl)-2-(2-diisopropylamino-ethylsulfanyl)-3H-quinazolin-4-one 
• 108534-25-4 2-(3-Amino-propylsulfanyl)-3-(3-chloro-phenyl)-3H-quinazolin-4-one 
• 108534-16-3 2-(2-Amino-ethylsulfanyl)-3-(3-chloro-phenyl)-3H-quinazolin-4-one 

Relevant academic research and scientific papers

A convenient and efficient synthesis of 2-thioxoquinazolinone derivatives via microwave irradiation

The synthesis of 2-thioxoquinazolinone derivatives was achieved by condensation of isatoic anhydride, primary amine, and carbon disulfide under microwave irradiation. This convenient and efficient method affords the desired products with good to excellent yields. Satisfactory infrared spectroscopy, 1H NMR, and high-resolution mass spectrometry (electrospray ionization) spectra were obtained for all compounds described.

Design, synthesis, antiproliferative and antibacterial evaluation of quinazolinone derivatives

A series of novel quinazolinone derivatives bearing a disulfide bond were designed and synthesized. Their in vitro antiproliferative activities were evaluated using CCK-8 assay against SMMC-7721, Hela, A549 and MCF-7 human cancer cell lines and normal cell lines L929. The preliminary bioassay results demonstrated that all compounds 7a–7h, 8a–8h and 9a–9h exhibited antiproliferation with various degrees, and some compounds showed better effects than positive control 5-fluorouracil against different cancer cell lines. Among these compounds, 8c and 9f showed significant antiproliferative activity against SMMC-7721 cells with IC50 values of 2.88 and 2.56 μM, respectively. In Hela cells, compounds 9c and 9d showed highly effective biological activity with IC50 values of 3.16 and 2.68 μM, respectively. Compounds 7a and 9a exhibited good inhibitory effect against A549 cells with IC50 values of 3.53 and 3.54 μM, respectively. In MCF-7 cells, compounds 7e, 8e and 9e displayed excellent activity with IC50 values of 1.26, 1.12 and 1.85 μM, respectively. Besides, most of the tested compounds showed low cytotoxic effect against the normal cell lines L929. Biological evaluation indicated that all the tested compounds possessed antibacterial activity with certain degrees.

Synthesis, in vitro, and in silico studies of newly functionalized quinazolinone analogs for the identification of potent α-glucosidase inhibitors

Functionalized quinazolinone derivatives 1–30 were synthesized by two-step reaction. First, anthranilic acid was treated with substituted phenyl isothiocyanate to synthesize 3-aryl-2-thioxo-2,3-dihydroquinazolinone derivatives 1–8 which in turn reacted with different bromoacetophenone derivatives to obtain fully functionalized quinazolinone derivatives 9–30. Both reactions were catalyzed by triethylamine. All the products were characterized by EI-, HREI-MS, 1H-, and 13CNMR spectroscopic techniques. All compounds were subjected to their in vitro α-glucosidase inhibitory activity. Results showed that except compound 1–3, 5, 7, and 22, all compounds were found potent and showed many folds increased α-glucosidase enzyme inhibition as compared to standard acarbose (IC50 = 750.0 ± 10.0?μM). Compound 13 (IC50 = 85.0 ± 0.5?μM) was recognized as the most potent analog of the whole series, with ninefold enhanced inhibitory potential than the standard acarbose. Compounds 1–9, 11, 12, 22, and 26 were structurally known compounds, while remaining all are new. Kinetic study on compound 13 showed that the compound is following a competitive-type inhibition mechanism. Furthermore, in silico studies have also been performed to better rationalize the interactions between synthetic compound and active site of the enzyme. Graphic abstract: [Figure not available: see fulltext.]

Identification of potent cholecystokinin-B receptor antagonists: Synthesis, molecular modeling and anti-cancer activity against pancreatic cancer cells

Advanced malignant stages of pancreatic cancer have poor prognosis and very few treatment strategies are available. Pancreatic cancer is known to possess unique growth-related receptors that when activated, stimulate tumour proliferation. Gastrin and its related peptide cholecystokinin (CCK) are also significantly involved in the growth of this cancer type as well as other malignancies through activation of the cholecystokinin-B receptor (CCK-BR). New treatment strategies with CCK-BR antagonists are being suggested that suppress the growth promoting effects of gastrin. In this paper, we report the development of two series of quinazolinone derivatives incorporating hydrazinecarbothioamide (compounds 3a-g) and the hydrazino group (compounds 4a-e) as linkers for developing CCK-BR antagonists. The affinities of the compounds were determined using docking into the CCK-BR homology modeled structure. The compounds were tested for in vitro CCK-BR binding and gastric acid secretion in an isolated lumen-perfused mouse stomach assay. The compounds exhibited CCK-BR binding activity (IC50) in the range of 0.2-975 nM and showed good gastric acid secretion inhibitory activity. Molecular modeling of the compounds was done and pharmacophore mapping results showed good prediction of in vitro activity which correlated well with the experimental antagonistic activity. The compounds were further tested for their cytotoxicity on CCK-BR expressing pancreatic cancer cells. The results of the study provided two potent CCK-BR antagonists which also possess good to moderate growth inhibitory activities against pancreatic cancer cells.

Synthesis and Anticonvulsant Activity Evaluation of 4-Phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one and Its Derivatives

A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones (6a-x) with triazole and other heterocyclic substituents (7-14) were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity by maximal electroshock (MES) and rotarod neurotoxicity tests. Among the compounds studied, 6o and 6q showed wide margins of safety with protective indices (PIs) that were much higher than those of currently used drugs (PI6o > 25.5, PI6q > 26.0). Compounds 6o and 6q showed significant oral activity against MES-induced seizures in mice, with ED50 values of 88.02 and 94.6 mg/kg, respectively. The two compounds were also found to have potent activity against seizures that were induced by pentylenetetrazole and bicuculline. A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones with triazole and other heterocyclic substituents were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity using maximal electroshock and rotarod neurotoxicity tests.

Development of thioquinazolinones, allosteric Chk1 kinase inhibitors

A high throughput screening campaign was designed to identify allosteric inhibitors of Chk1 kinase by testing compounds at high concentration. Activity was then observed at Km for ATP and at near-physiological concentrations of ATP. This strategy led to the discovery of a non-ATP competitive thioquinazolinone series which was optimized for potency and stability. An X-ray crystal structure for the complex of our best inhibitor bound to Chk1 was solved, indicating that it binds to an allosteric site ～13 A from the ATP binding site. Preliminary data is presented for several of these compounds.

Some ring closure reactions with cyanothioformamides: New route for the synthesis of (imidazolidine, oxazolidine & pyrroline)-iminothiones, benzothiazoloquinazolinones and imidazoquinoxalines

Cyanothioformamides were reacted with isocyanates, isothiocyanates, aldehydes, acetylenedicarboxylic acid and anthranilic acids to produce imidazolidines, oxazolidines pyrroline, quinazolinones and benzothiazoloquinazolinones, respectively. Interaction of imidazolidineimino(thiones and dithiones) with o-phenylenediamines gave rise to imidazoquinoxalines and imidazoquinoxalinethiones, respectively.

Synthesis and Antibacterial Activity of 2-thio>-3-aryl(or alkyl)-6,8-disubstituted-4(3H)-quinazolinones

Synthesis of 47 new 2-thio>-3-aryl(or alkyl)-6,8-disubstituted-4(3H)-quinazolinones, 2-6, from the corresponding 2-thio-4(3H)-quinazolinones, 1, has been described.Fifteen of them were screened for their antibacterial activity by t