17329-31-6

Basic information

• Product Name: 6-AMINO-3H-QUINAZOLIN-4-ONE
• Synonyms: 6-amino-4(3h)-quinazolinone;6-AMINO-3H-QUINAZOLIN-4-ONE;6-AMINO-4-HYDROXYQUINAZOLINE;6-AMINO-4(1H)-QUINAZOLINONE;6-AMINO-4-QUINAZOLINONE;ASINEX-REAG BAS 10150436;6-Amino-3H-quinazoline-4-one;6-Amino-3H-quinazolin-4-one 6-Amino-4-quinazolinone
• CAS NO: 17329-31-6
• Molecular Formula: C₈H₇N₃O
• Molecular Weight: 161.16
• Product Categories: pharmacetical;API intermediates
• Mol File: 17329-31-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 303 °C(Solv: water (7732-18-5))
• Boiling Point: 421.1 °C at 760 mmHg
• Flash Point: 208.5 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 2.67E-07mmHg at 25°C
• Refractive Index: 1.734
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.95±0.20(Predicted)
• CAS DataBase Reference: 6-AMINO-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-3H-QUINAZOLIN-4-ONE(17329-31-6)
• EPA Substance Registry System: 6-AMINO-3H-QUINAZOLIN-4-ONE(17329-31-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 17329-31-6(Hazardous Substances Data)

Usage

General Description

6-Amino-3H-quinazolin-4-one, also known as 3H-quinazolin-4-one, 6-amino-, is a chemical compound with the molecular formula C8H6N4O. It is a heterocyclic compound that contains a quinazolin-4-one core with an amino group at the 6 position. 6-AMINO-3H-QUINAZOLIN-4-ONE is a stable solid that is commonly used in the pharmaceutical industry as a building block for the synthesis of various biologically active compounds and pharmaceutical drugs. Its properties and use make it an important compound in drug discovery and development, particularly in the design and synthesis of new potential therapeutics for various medical conditions.

InChI:InChI=1/C8H7N3O/c9-5-1-2-7-6(3-5)8(12)11-4-10-7/h1-4H,9H2,(H,10,11,12)

Upstream product

• 6943-17-5 6-nitroquinazolone 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 17420-30-3 5-nitroanthranilonitrile 
• 91-56-5 indole-2,3-dione 
• 611-09-6 5-nitroisatin 
• 16064-13-4 6-nitro-3-methyl-quinazolin-4-one 
• 6943-17-5 6-nitroquinazolin-4-ol 
• 4693-02-1 6-nitroisatoic anhydride 

Downstream Products

• 118895-90-2 di-tert-butyl 2-desamino-5,8-dideazaisofolate 
• 1334953-74-0 6-[5-({[2-(methylsulphonyl)ethyl]amino}methyl)furan-2-yl]quinazolin-4-ol 
• 1618648-59-1 N-((5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-yl)methyl)-2,2,2-trifluoro-N-(2-(methylsulfonyl)ethyl)acetamide 
• 388082-78-8 lapatinib ditosylate 
• 1036390-09-6 C₁₈H₁₇N₃O₅ 
• 118895-95-7 2-desamino-5,8-dideazaisofolic acid 

Relevant articles and documents

Synthesis and Cytotoxicity of Quinazolin-4(3H)-one Based Peptides

Abstract: A novel series of quinazolin-4(3H)-one derivatives has been synthesized in high yields using the multicomponent Ugi reaction and characterized by IR, NMR and mass spectral data. The products have been tested for their cytotoxic activity against HeLa cells. Two tested compounds have shown potent activity compared to standard drug Doxorubicin. The in silico docking studies of the compounds against quinone reductase-2 (4ZVM) enzyme have also supported their activity.

PROCESS FOR THE PREPARATION OF LAPATINIB

Present process relates to an improved and commercial process for the preparation of lapatinib of formula-I or its pharmaceutically acceptable p-toluenesulfonate salt involving novel intermediates of formulae-XVII, XVIII, and XIX. Present process utilizes Meerwein reaction as a key step in the aryl C-C bond formation step avoiding costly boronate coupling chemistry used in the conventional synthesis of lapatinib.

Synthesis and SAR optimization of quinazolin-4(3H)-ones as poly(ADP-ribose)polymerase-1 inhibitors

We have demonstrated that quinazolin-4(3H)-one, a nicotinamide (NI) mimic with PARP-1 inhibitory activity in the high micromolar range (IC50 = 5.75 μM) could be transformed into highly active derivatives with only marginal increase in molecular weight. Convenient one to two synthetic steps allowed us to explore extensive SAR at the 2-, and 5- through 8-positions of the quinazolin-4(3H)-one scaffold. Substitutions at the 2- and 8-positions were found to be most favorable for improved PARP-1 inhibition. The amino group at 8-position resulted in compound 22 with an IC50 value of 0.76 μM. Combination of the 8-amino substituent with an additional methyl substituent at the 2-position provided the most potent compound 31 [8-amino-2-methylquinazolin- 4(3H)-one, IC50 = 0.4 μM] in the present study. Compound 31 inhibited the proliferation of Brca1-deficient cells with an IC50 value of 49.0 μM and displayed >10-fold selectivity over wild type counterparts. Binding models of these derivatives within the active site of PARP-1 have further supported the SAR data and will be useful for future lead optimization efforts.