607-19-2

Basic information

• Product Name: 3-METHYLQUINAZOLINE-2,4(1H,3H)-DIONE
• Synonyms: 3-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione;2,4(1H,3H)-Quinazolinedione, 3-methyl-;3-methyl-1H-quinazoline-2,4-dione;3-methyl-1H-quinazoline-2,4-quinone
• CAS NO: 607-19-2
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.18
• Mol File: 607-19-2.mol

Chemical Properties

• Melting Point: 236-238 °C
• Appearance: /
• Density: 1.292g/cm³
• Refractive Index: 1.585
• Storage Temp.: 2-8°C
• PKA: 12.85±0.20(Predicted)
• CAS DataBase Reference: 3-METHYLQUINAZOLINE-2,4(1H,3H)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLQUINAZOLINE-2,4(1H,3H)-DIONE(607-19-2)
• EPA Substance Registry System: 3-METHYLQUINAZOLINE-2,4(1H,3H)-DIONE(607-19-2)

Safety Data

• Hazardous Substances Data: 607-19-2(Hazardous Substances Data)

Usage

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

Upstream product

• 186581-53-3 diazomethane 
• 86-96-4 1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 57212-70-1 N-(mesyloxy)phthalimide 
• 74-89-5 methylamine 
• 56788-11-5 N-methyl-phthalamide 
• 124-38-9 carbon dioxide 
• 118988-18-4 N-methyl o-(triphenylphosphoranylidene)amino benzamide 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 118-48-9 isatoic anhydride 
• 57-13-6 urea 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 598-50-5 N-Methylurea 
• 85-44-9 phthalic anhydride 

Downstream Products

• 607-68-1 2,4-dichloroquinazoline 
• 1206117-96-5 3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-6-sulfonyl chloride 
• 1196453-25-4 C₁₆H₁₄N₂O₂S 
• 1196453-29-8 C₁₆H₁₁F₃N₂O₂ 
• 1196453-26-5 C₁₇H₁₇N₃O₂ 
• 1196453-30-1 C₁₆H₁₂N₂O₄ 
• 39602-30-7 1-(4-methoxyphenyl)-3-methylquinazoline-2,4(1H,3H)-dione 

Relevant articles and documents

Synthesis and evaluation of highly selective quinazoline-2,4-dione ligands for sphingosine-1-phosphate receptor 2

A series of twenty-nine new quinazoline-2,4-dione compounds were synthesized and their IC50 values for binding toward sphingosine-1-phosphate receptor 2 (S1PR2) were determined using a [32P]S1P binding assay. Seven compounds 2a, 2g, 2h, 2i, 2j, 2k, and 5h exhibit high S1PR2 binding potencies (IC50 values 98%), and high molar activity (153-222 GBq μmol-1, at the end of bombardment). [11C]2a and [11C]2i were further evaluated by the ex vivo biodistribution study. The results showed that both tracers have low brain uptake, preventing their potential for neuroimaging application. Further explorations of this class of S1PR2 PET tracers in peripheral tissue diseases are underway. This journal is

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.

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4- dihydroquinazolin-2-ylthio) acetohydrazide 6. {figure presented}.

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.

Synthesis of 3-methylquinazolin-4(3H)-one derivatives

Oxidation of 3-methyl-2-sulfanylquinazolin-4(3H)-one with chlorine dioxide under different conditions gave 2,2'-disulfanediylbis[3-methylquinazolin-4(3H)- one], 3-methyl-4-oxo-3,4-dihydroquinazoline-2-sulfonic acid, 3-methylquinazoline-2,4(1H,3H)-dione, 6

Synthesis of novel quinazoline-4-one derivatives and their acyclonucleoside analogs

A number of quinazolin-4-one derivatives were synthesized. Reaction of the 2-hydrazonoquinazoline-4-one derivatives with aldoses afforded the corresponding sugar hydrazones which on treatment with ferric chloride to afford the corresponding acyclic nucleoside analogues.

Metal and phosgene-free synthesis of 1H-quinazoline-2,4-diones by selenium-catalyzed carbonylation of o-nitrobenzamides

1H-Quinazoline-2,4-diones were efficiently synthesized by selenium-catalyzed carbonylation of o-nitrobenzamides under relatively mild conditions. In situ-generated carbonyl selenide (SeCO) is proposed to initiate the catalytic carbonylation. Thus, a concise transition metal and phosgene-free synthetic route to potentially bioactive-substituted 1H-quinazoline-2,4-dione derivatives has been developed.

Room-temperature palladium-catalyzed C-H activation: Ortho-carbonylation of aniline derivatives

Pd and CO - ureally got me! The title reaction proceeds efficiently at 18°C under CO (1 atm) with 5 % [Pd(OTs)2 (MeCN)2] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ=benzoquinone, Ts=4-toluenesulfonyl).

Copper-mediated N-arylation of quinazolinediones

A mild, ligand-free method of arylating 2,4-quinazolinediones using arylboronates in the presence of copper salts is described. The reaction is tolerant of a variety of functional groups and works for arylboronic acid, arylboronic ester, and aryltrifluoro

Traceless synthesis of quinazoline-2,4-diones by curtius rearrangement reaction using poly(ethylene glycol) as soluble polymeric support

(Chemical Equation Presented) We have developed an efficient method to synthesize various quinazoline-2,4-diones using polyethylene glycol) as soluble polymeric support. The procedure of this reaction included: formation of acyl azide, efficient Curtius rearrangement, nucleophlic addition with amines to produce ureas, cyclization and concurrent cleavage of the resulted six-membered heterocycle from PEG-support in excellent yields. This method is mild and manipulation is easy.