1898-06-2

Basic information

• Product Name: 2-METHYL-3-AMINO-4-QUINAZOLONE
• Synonyms: IFLAB-BB F0307-0682;ASISCHEM W61338;2-METHYL-3-AMINO-4-QUINAZOLONE;3-AMINO-2-METHYL-3,4-DIHYDROQUINAZOLIN-4-ONE;3-AMINO-2-METHYL-3 H-QUINAZOLIN-4-ONE;3-AMINO-2-METHYL-4(3H)QUINAZOLINONE;AKOS B028736;AKOS AU36-M15
• CAS NO: 1898-06-2
• Molecular Formula: C₉H₉N₃O
• Molecular Weight: 175.19
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinazolines
• Mol File: 1898-06-2.mol
• Article Data: 54

Chemical Properties

• Melting Point: 149-152 °C(lit.)
• Boiling Point: 348.1 °C at 760 mmHg
• Flash Point: 164.4 °C
• Appearance: /
• Density: 1.35 g/cm³
• PKA: -0.13±0.70(Predicted)
• CAS DataBase Reference: 2-METHYL-3-AMINO-4-QUINAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-3-AMINO-4-QUINAZOLONE(1898-06-2)
• EPA Substance Registry System: 2-METHYL-3-AMINO-4-QUINAZOLONE(1898-06-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1898-06-2(Hazardous Substances Data)

Usage

Uses

3-Amino-2-methyl-4(3H)quinazolinone may be used to synthesize:2-methyl-3-[3′-aminophthalimido]-4(3H)-quinazolinone2-alkyl-3-(methylamino)-4(3H)-quinazolinone3-amino-2-chloromethyl-4(3H)-quinazolinone

General Description

3-Amino-2-methyl-4(3H)quinazolinone is a quinazoline derivative. 2-Methyl-3,1-benzoxazin-4-one undergoes condensation reaction with hydrazine hydrate to yield 3-amino-2-methyl-4(3H)quinazolinone. It undergoes condensation with various substituted aldehydes to afford Schiff′s bases.

Upstream product

• 20628-20-0 ethyl N-acetylanthranilate 
• 1769-24-0 2-methyl-4-quinazolone 
• 64-19-7 acetic acid 
• 28864-26-8 acetylhydrazide de l'acide anthranilique 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 141-97-9 ethyl acetoacetate 
• 1904-58-1 anthranilic acid hydrazide 
• 2719-08-6 methyl 2-(acetylamino)benzoate 
• 10073-94-6 4-(2-methyl-4-oxoquinazoline-3-yl)benzoic acid hydrazide 
• 118-92-3 anthranilic acid 
• 54789-69-4 2-methyl-4H-benzo[1,3]oxazin-4-one 
• 25380-20-5 2-cyano-N-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide 
• 60-35-5 acetamide 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 56158-74-8 2-methyl-3-(phenylmethylene)-amino-4(3H)quinazolinone 
• 94066-20-3 2-methyl-3-(2'-hydroxybenzylamino)-quinazolin-(3H)-4-one 
• 160562-20-9 N-phenyl-3-(2'-methyl-4'(3'H)-quinazolinon-3'-yl)aminocarbamide 
• 93332-51-5 3-(4-hydroxy-3-methoxy-benzylideneamino)-2-methyl-3H-quinazolin-4-one 
• 107621-91-0 4-acetylamino-benzoic acid-(2-methyl-4-oxo-4H-quinazolin-3-ylamide) 
• 41332-45-0 2-methyl-3-(3-phenyl-allylideneamino)-3H-quinazolin-4-one 
• 26107-21-1 2-Methyl-3-((1R,2R)-2-phenyl-aziridin-1-yl)-3H-quinazolin-4-one 
• 26107-21-1 2-Methyl-3-((1R,2S)-2-phenyl-aziridin-1-yl)-3H-quinazolin-4-one 
• 26107-21-1 1-(3,4-dihydro-2-methyl-4-oxoquinazolin-3-yl)-2-phenylaziridine 
• 1769-24-0 2-methyl-4-quinazolone 
• 93681-93-7 3-((1R,2R)-2-Butyl-aziridin-1-yl)-2-methyl-3H-quinazolin-4-one 
• 141736-11-0 3-(diphenylmethyleneamino)-2-methylquinazolin-4(3H)-one 
• 150391-49-4 2-Methyl-3-{[1-(2-phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-3H-quinazolin-4-one 
• 98832-91-8 3-(o-iodobenzoylamino)-2-methyl-4(3H)-quinazolone 

Relevant articles and documents

Cytotoxicity and Antibacterial Evaluation of O-Alkylated/Acylated Quinazolin-4-one Schiff Bases

A series of quinazolin-4-one Schiff bases were synthesized and tested in vitro for their cytotoxicity against two cancerous cell lines (MCF-7, Caco-2) and a human embryonic cell line (HEK-293) including their antibacterial evaluation against two Gram-positive and four Gram-negative bacterial strains. Most of the quinazoline-Schiff bases exhibited potent cytotoxicity against Caco-2. 3-[(Z)-({4-[(But-2-yn-1-yl)oxy]phenyl}methylidene)amino]-2-methylquinazolin-4(3H)-one (6f) with the O-butyne functional group displayed three-fold higher cytotoxic activity (IC50=376.8 μM) as compared to 5-fluorouracil (5-FU; IC50=1086.1 μM). However, all compounds were found to be toxic to HEK-293, except for 3-[(Z)-({4-[(2,4-difluorophenyl)methoxy]phenyl}methylidene)amino]-2-methylquinazolin-4(3H)-one (6h) that showed ～three-fold lower toxicity and higher selectivity index than 5-FU. Structure–activity relationship (SAR) analysis revealed that O-alkylation generally increased the anticancer activity and selectivity of quinazoline-4-one Schiff bases toward Caco-2 cells. The fluorinated Schiff-base generally exhibited even more significant cytotoxic activity compared to their chlorine analogs. Surprisingly, none of the quinazoline-4-one Schiff bases displayed encouraging antibacterial activity against the bacterial strains investigated. Most of the compounds were predicted to show compliance with the Lipinski parameters and ADMET profiles, indicating their drug-like properties.

N-amination of 4-pyrimidones by mesitylenesulfonyl hydroxylamine

The 3-amino derivatives are formed exclusively during the amination of the anions of 6-methyl-4-pyrimidones and 2-methyl-4-quinazolone by mesitylenesulfonyl hydroxylamine.

Synthesis of Some Quinazolinone Derivatives Functionalized with N-3 Heterocyclic Side Chain

A number of quinazolinone derivatives substituted at position-3 are prepared from 3, 1-benzoxazinone. Thus, treatment of 3, 1-benzoxazinon with cyanoacetohydrazide or thionocarbohydrazide gave the quinazolinone derivatives. The quinazolinones have been utilized as synthon for new pyridinone, azete, thiazole, thiazolidinone, thosemicarbazide, and thiosemicarbazone derivatives. The structures of the synthesized compounds were established on the basis of IR, 1HNMR, mass spectral data, and elemental analyses.

Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold

For the first time, quinazolin-4(3H)-one-based cationic surfactants were prepared and fully characterized by IR and NMR spectroscopic techniques and elemental analysis. Some of their physicochemical properties, such as density, critical micelle concentrat

Synthesis and evaluation of anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities of some 3H-quinazolin-4-one derivatives

Some new 3H-quinazolin-4-one derivatives were synthesised and screened for anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities. Compound 15d was more potent in reducing the cell viabilities of HT-29 and SW620 cells lines to 38%, 36.7%, compared to 5-FU which demonstrated cell viabilities of 65.9 and 42.7% respectively. The IC50 values of 15d were ～20?μg/ml. Assessment of apoptotic activity revealed that 15d decreased the cell viability by down regulating Bcl2 and BclxL. Moreover, compounds, 8j, 8d/15a/15e, 5b, and 8f displayed lowered IC50 values than oleanolic acid against proinflammatory isoforms of hGV, hG-X, NmPLA2, and AmPLA2. In addition, 8d, 8h, 8j, 15a, 15b, 15e, and 15f showed better anti-α-amylase than quercetin, whereas 8g, 8h, and 8i showed higher anti-α-glucosidase activity than allopurinol. Thus, these compounds can be considered as potential antidiabetic agents. Finally, none of the compounds showed higher antiproteases or xanthine oxidase activities than the used reference drugs.