600718-11-4

Upstream product

• 40545-33-3 2-amino-5-methylbenzamide 
• 103-72-0 phenyl isothiocyanate 
• 105-36-2 ethyl bromoacetate 
• 2941-78-8 2-Amino-5-methylbenzoic acid 

Downstream Products

• 1412904-37-0 C₂₅H₁₈N₄O₄S 
• 1412904-38-1 N-(3,4,5,6-tetrachlorophthalimido)-2-[(3-phenyl-6-methyl-4-oxo-3H-quinazolin-2-yl)-thio]acetamide 
• 1412904-39-2 C₂₅H₁₄Br₄N₄O₄S 
• 1412904-40-5 N-(1,8-naphthalimido)-2-[(3-phenyl-4-oxo-6-methyl-3H-quinazolin-2-yl)-thio]acetamide 
• 1412904-35-8 2-hydrazinyl-6-methyl-3-phenyl-quinazolin-4(3H)-one 
• 80195-32-0 2-hydrazinyl-6-methyl-quinazolin-4(3H)-one 
• 80195-28-4 3-amino-2-hydrazino-6-methylquinazolin-4-(3H)-one 
• 1593583-15-3 6-methyl-3-phenylquinazolin-4(3H)-one 
• 211562-86-6 2-[(6-methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio]acetohydrazide 

Relevant academic research and scientific papers

2-thioquinazolinone compound and preparation method and application thereof

The invention provides a 2-thioquinazolinone compound and a preparation method and application thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: mixing an anthranilamide compound, an isothiocyanate compound, a bromide and a polar organic solvent, and carrying out a series cyclization reaction in an air atmosphere to obtain the 2-thioquinazolinone compound. According to the preparation method, the 2-thioquinazolinone compound can be prepared by one-step reaction without adding a catalyst, the yield and the purity of the product are high, the reaction route is simple, the operation is simple, and the preparation method is suitable for industrial production.

Synthesis, anticancer and apoptosis-inducing activities of quinazoline–isatin conjugates: epidermal growth factor receptor-tyrosine kinase assay and molecular docking studies

A new series of quinazolinone compounds 16–34 incorporating isatin moieties was synthesized. The antitumor efficacy of the compounds against MDA-MB-231, a breast cancer cell line, and LOVO, a colon cancer cell line, was assessed. Compounds 20, 21, 22, 23, 25, 27, 28, 29, 30, 31, 32, 33, and 34 displayed potent antitumor activity against MDA-MB-231 and LOVO cells (IC50: 10.38–38.67 μM and 9.91–15.77 μM, respectively); the comparative IC50 values for 5-fluorouracil and erlotinib in these cells lines were 70.28 μM, 22.24 μM and 15.23 μM, 25.31 μM respectively. The EGFR-TK assay and induction of apoptosis for compound 31 were investigated to assess its potential cytotoxic activity as a representative example of the novel synthesized compounds. At a concentration of 10 μM, compound 31 exhibited efficient inhibitory effect against EGFR-TK and induced apoptosis in MDA-MB-231 cells. Furthermore, a molecular docking study for compound 31 and erlotinib was performed to verify the binding mode toward the EGFR kinase enzyme, and showed a similar interaction as that with erlotinib alone. Graphical Abstract: Compound 31 showed potent antitumor activity and efficient inhibitory effect against EGFR-TK and induced apoptosis of MDA-MB-231 cells at a concentration of 10 μM.

Synthesis, antitumor and antimicrobial activity of some new 6-methyl-3-phenyl-4(3H)-quinazolinone analogues: in silico studies

Some new derivatives of substituted-4(3H)-quinazolinones were synthesized and evaluated for their in vitro antitumor and antimicrobial activities. The results of this study demonstrated that compound 5 yielded selective activities toward NSC Lung Cancer EKVX cell line, Colon Cancer HCT-15 cell line and Breast Cancer MDA-MB-231/ATCC cell line, while NSC Lung Cancer EKVX cell line and CNS Cancer SF-295 cell line were sensitive to compound 8. Additionally, compounds 12 and 13 showed moderate effectiveness toward numerous cell lines belonging to different tumor subpanels. On the other hand, the results of antimicrobial screening revealed that compounds 1, 9 and 14 are the most active against Staphylococcus aureus ATCC 29213 with minimum inhibitory concentration (MIC) of 16, 32 and 32 μg/mL respectively, while compound 14 possessed antimicrobial activities against all tested strains with the lowest MIC compared with other tested compounds. In silico study, ADME-Tox prediction and molecular docking methodology were used to study the antitumor activity and to identify the structural features required for antitumor activity.

Novel 4(3H)-quinazolinone analogs: Synthesis and anticonvulsant activity

A new series of quinazoline analogs was designed, synthesized, and evaluated for their anticonvulsant activity. Compounds 6, 12, 21, 36, 37, and 38 showed 70-100 % protection against PTZ-induced seizures acting as GABA A receptor agonists. Compound N-(3,4,5,6-tetrachloro-phthalimido)-2- [(3-phenyl-4-oxo-6-methyl-3H-quinazolin-2-yl)-thio]acetamide (12) representing the moderate active compounds and 2-[6-iodo-4-oxo-2-(thiophen-2-yl)-quinazolin- 3(4H)-yl]-isoindoline-1,3-dione (38) representing the remarkably active compounds in this stud, showed ED50 values of 457 and 251 mg/kg; TD50 values of 562 and 447 mg/kg; PI values of 1.22 and 1.78, LD 50 values of 1,288 and 1,380 mg/kg, and TI values of 2.82 and 5.50, respectively. Compound 38 proved to be almost twofold more active than the standard drug sodium valproate.

Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)-quinazolinone-2-yl)mercaptoacetyl]hydrazono]-1H-2- indolinones

New esters (2b and 2c) and hydrazides (3b and 3c) were synthesized from 6-methyl/fluoro-3-phenyl-4(1H, 3H)-quinazolinone-2-thiones (1b and 1c). Subsequent treatment of 3-phenyl-4(3H)-quinazolinone-2-yl)mercaptoacetic acid hydrazides (3a-e) with 1H-indole-