604-50-2

Basic information

• Product Name: 1-methylquinazoline-2,4(1H,3H)-dione
• Synonyms: 1-methylquinazoline-2,4(1H,3H)-dione;1-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione;1-Methyl-2,4(1H,3H)-quinazolinedione;1-Methyl-5,6-[1,3]butadienopyrimidine-2,4(1H,3H)-dione;Glycosmicine;1-methyl-2,4(1H,3H)-quinazolinedione(SALTDATA: FREE);1-methylquinazoline-2,4-dione;1-methylquinazoline-2,4-quinone
• CAS NO: 604-50-2
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.18
• Mol File: 604-50-2.mol

Chemical Properties

• Appearance: /
• Density: 1.292 g/cm³
• Refractive Index: 1.585
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1-methylquinazoline-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methylquinazoline-2,4(1H,3H)-dione(604-50-2)
• EPA Substance Registry System: 1-methylquinazoline-2,4(1H,3H)-dione(604-50-2)

Safety Data

• Hazardous Substances Data: 604-50-2(Hazardous Substances Data)

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

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

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 
• 1400799-32-7 N-(2-chlorobenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-33-8 N-(2-methylbenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-34-9 N-(4-nitrobenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-37-2 N-(4-methoxybenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-38-3 N-(4-methylbenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-39-4 N-(3-nitrobenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-40-7 N-(4-chlorobenzoyl)glycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 
• 1400799-30-5 N-benzoylglycine-2-(1,4-dihydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl)ethyl ester 

Relevant articles and documents

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.

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.

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.

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.

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.

Synthesis and antioxidant activity of novel quinazolinones functionalized with urea/thiourea/thiazole derivatives as 5-lipoxygenase inhibitors

In the present study, a series of novel quinazolinones functionalized with urea/thiourea/thiazole derivatives was synthesized and evaluated for their antioxidant and 5-lipoxygenase (5-LOX) inhibition activities. The newly synthesized compounds were characterized using 1H NMR, 13C NMR, IR, Mass spectra and elemental analysis. The antioxidant activities of the title compounds were evaluated using DPPH, superoxide, hydroxyl and nitric oxide radical scavenging assay in vitro. It is revealed from the antioxidant screening results that the compounds 3e, 5f and 6c manifested profound antioxidant potential. The synthesized compounds were screened for their 5-LOX inhibitory activity. Overall, 3e, 5f and 6c showed promising antioxidant and 5f showed 5-LOX inhibitory activity and may be used as the lead compounds in the future study.

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.