604-50-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1-methylquinazoline-2,4(1H,3H)-dione is utilized as a building block in the synthesis of pharmaceuticals and agrochemicals, serving as a key intermediate for creating biologically active compounds targeting a range of diseases and pests.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-methylquinazoline-2,4(1H,3H)-dione is employed as a scaffold for developing drugs. Its molecular structure allows for the design of compounds that can target various diseases, making it a valuable asset in drug discovery and development.
Used in Materials Science:
1-methylquinazoline-2,4(1H,3H)-dione has been investigated for its potential applications in materials science, particularly in the development of organic electronic and optoelectronic devices. Its unique properties contribute to the advancement of these technologies, enhancing their performance and capabilities.

InChI:InChI=1/C9H8N2O2/c1-11-7-5-3-2-4-6(7)8(12)10-9(11)13/h2-5H,1H3,(H,10,12,13)

Upstream product

• 590-28-3 potassium cyanate 
• 119-68-6 N-Methylanthranilic acid 
• 7505-81-9 2-methylaminobenzamide 
• 541-41-3 chloroformic acid ethyl ester 
• 57-13-6 urea 
• 74-88-4 methyl iodide 
• 86-96-4 1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 7664-93-9 sulfuric acid 
• 917-61-3 sodium isocyanate 
• 85-91-6 Methyl N-methylanthranilate 
• 134-20-3 2-carbomethoxyaniline 
• 10328-92-4 N-Methylisatoic anhydride 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 246264-31-3 (+/-)-N-methyl-2-[2-(1-methylquinazolin-2,4-dione-3-yl)ethyl]-N-(4-phenoxybenzenesulfonyl)glycine allyl ester 
• 1296731-98-0 C₁₆H₁₂N₂O₃ 
• 1296732-00-7 C₁₇H₁₄N₂O₃ 
• 1296732-02-9 C₁₇H₁₄N₂O₄ 
• 1296732-06-3 C₁₆H₁₁N₃O₅ 
• 1296732-04-1 C₁₆H₁₁BrN₂O₃ 
• 1436384-11-0 3-(3-(2-hydroxyphenylamino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-12-1 3-(3-(3-hydroxyphenylamino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-13-2 3-(3-(4-hydroxyphenylamino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-14-3 3-(3-((2-hydroxy-5-nitrophenyl)amino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-15-4 3-(3-((4-methoxy-2-nitrophenyl)amino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-16-5 3-(3-((4-aminophenyl)amino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-17-6 3-(3-((3-bromo-4-methylphenyl)amino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 
• 1436384-18-7 3-(3-((3-chlorophenyl)amino)propanoyl)-1-methylquinazoline-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Quinazolines. 2*. unsymmetric 1,3-dialkyl-6-chlorosulfonyl- quinazoline-2,4-diones in nucleo- philic substitution reactions

The corresponding 6-chlorosulfonylquinazoline-2,4-diones were synthesized by the reactions of 1-methylquinazoline-2,4-dione and its 3-alkyl-substituted derivatives with chlorosulfonic acid. Treatment of the products with nucleophilic agents (water or ammo

Quantum chemical investigation of the effect of cation size on the course of the methylation of 2,4-dioxoquinazoline salts

The effect of cation size on the dual reactivity of the lithium, sodium, and potassium salts of 2,4-dioxoquinazolines in liquid and solid phase methylation reactions has been studied. The results obtained were confirmed by data of quantum chemical calculations and IR spectroscopy. 1997 Plenum Publishing Corporation.

Design, synthesis and biological evaluation of novel quinazoline-2,4-diones conjugated with different amino acids as potential chitin synthase inhibitors

A series of (2-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl) acetamido) acids) (6 a-m), (7) has been designed to inhibit the action of fungus chitin synthase enzyme (CHS). The synthesis of the designed compounds was carried out in four steps starting from the reaction between 1-methylquinazoline-2,4(1H,3H)-dione and ethyl chloroacetate to yield the ethyl acetate derivative. This ester was hydrolyzed to the corresponding carboxylic acid derivative that was then utilized to couple several amino acids getting the final designed compounds. The synthesized compounds were tested for their inhibition against CHS. Compound 7 showed the highest potency among others with minimum inhibitory concentration (IC50) of 0.166 mmol/L, while polyoxin B (the positive control) had IC50 of 0.17 mmol/L. The synthesized compounds were also evaluated for their in vitro antifungal activity using Aspergillus fumigates, Aspergillus flavus, Crytococcus neoformans and Candida albicans. Unfortunately, the 14 synthesized compounds showed lower in vitro activity compared to the used active controls. However, compound 6m and fluconazole have synergistic effect on Aspergillus flavus; Compounds 7 and fluconazole have synergistic effects on Aspergillus fumigates.

2-QUINOLONE DERIVED INHIBITORS OF BCL6

The present invention relates to compounds of formula I that function as inhibitors of BCL6(B- cell lymphoma 6) activity: Formula I wherein X1, X2, X3, R1, R2, R3, R4 and R5 are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer,as well as other diseases or conditions in which BCL6 activity is implicated.

Cell-Active Small Molecule Inhibitors of the DNA-Damage Repair Enzyme Poly(ADP-ribose) Glycohydrolase (PARG): Discovery and Optimization of Orally Bioavailable Quinazolinedione Sulfonamides

DNA damage repair enzymes are promising targets in the development of new therapeutic agents for a wide range of cancers and potentially other diseases. The enzyme poly(ADP-ribose) glycohydrolase (PARG) plays a pivotal role in the regulation of DNA repair mechanisms; however, the lack of potent drug-like inhibitors for use in cellular and in vivo models has limited the investigation of its potential as a novel therapeutic target. Using the crystal structure of human PARG in complex with the weakly active and cytotoxic anthraquinone 8a, novel quinazolinedione sulfonamides PARG inhibitors have been identified by means of structure-based virtual screening and library design. 1-Oxetan-3-ylmethyl derivatives 33d and 35d were selected for preliminary investigations in vivo. X-ray crystal structures help rationalize the observed structure-activity relationships of these novel inhibitors.

HYDROXYL PURINE COMPOUNDS AND USE THEREOF

Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers thereof or pharmaceutically acceptable salts thereof.

VMAT INHIBITORY COMPOUNDS

Disclosed herein are compounds that bind to the vesicular monoamine transporter 2 (VMAT2), pharmaceutical compositions comprising those compounds, and methods of treatment using said compounds and pharmaceutical compositions.

2,4-DIOXO-QUINAZOLINE-6-SULFONAMIDE DERIVATIVES AS INHIBITORS OF PARG

The present invention relates to compounds of formula I that function as inhibitors of PARG (Poly ADP-ribose glycohydrolase) enzyme activity wherein R1a, R1b, R1c, R1d, R1e, W, X1, X2, X3, X4, X5, X6, X7, c are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which PARG activity is implicated.

Design, synthesis, and evaluation of novel 1-methyl-3-substituted quinazoline-2,4-dione derivatives as antimicrobial agents

A series of novel 1-methyl-3-substituted quinazoline-2,4-dione derivatives was designed, synthesized, and evaluated for their antimicrobial activities against six strains of bacteria and five fungi in vitro. The synthesized compounds were characterized by spectral methods. The bioactive assays showed that most of the compounds exhibited moderate antimicrobial activities against the tested strains. Springer Science+Business Media 2013.

Design, synthesis and evaluation of novel quinazoline-2,4-dione derivatives as chitin synthase inhibitors and antifungal agents

A series of novel 1-methyl-3-substituted quinazoline-2,4-dione derivatives were designed, synthesized, and characterized by 1H NMR, 13C NMR and MS spectral data. Their inhibition against chitin synthase (CHS) and antifungal activities were evaluated in vitro. Results showed compounds 5b, 5c, 5e, 5f, 5j, 5k, 5l, and 5o had strong inhibitory potency against CHS. Compound 5c, which has the highest potency among these compounds, had a half-inhibition concentration (IC50) of 0.08 mmol/L, while polyoxin B as positive drug had IC50 of 0.18 mmol/L. These IC 50 values of compounds 5i, 5m, 5n, and 5s were greater than 0.75 mmol/L, which revealed that those compounds had weak inhibition activity against CHS. Moreover, most of these compounds exhibited moderate to excellent antifungal activities. In detail, to Candida albicans, the activities of compound 5g and 5k were 8-fold stronger than that of fluconazole and 4-fold stronger than that of polyoxin B; to Aspergillus flavus, the activities of 5g, 5l and 5o were16-fold stronger than that of fluconazole and 8-fold stronger than that of polyoxin B; to Cryptococcus neoformans, the minimum-inhibition- concentration (MIC) values of compounds 5c, 5d, 5e and 5l were comparable to those of fluconazole and polyoxin B. The antifungal activities of these compounds were positively correlated to their IC50 values against CHS. Furthermore, these compounds had negligible actions to bacteria. Therefore, these compounds were promising selective antifungal agents.