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

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

Uses

Used in Pharmaceutical Industry:
6-Amino-3H-quinazolin-4-one is utilized as a synthetic building block for the creation of biologically active compounds. Its presence in the molecular structure of various drugs allows for the exploration of its potential therapeutic effects against different diseases and conditions.
Used in Drug Discovery and Development:
In the realm of drug discovery, 6-Amino-3H-quinazolin-4-one serves as a crucial component in the design of new potential therapeutics. Its unique structure and properties make it a valuable asset in the development of innovative medications aimed at treating a range of medical conditions.
Used in Synthesis of Biologically Active Compounds:
6-Amino-3H-quinazolin-4-one is employed as a key intermediate in the synthesis of biologically active compounds. Its integration into these compounds can enhance their pharmacological properties, potentially leading to more effective treatments.
Used in Research and Development of New Therapeutics:
6-Amino-3H-quinazolin-4-one is used in research for the development of new therapeutics. Its role in the synthesis of novel compounds allows scientists to investigate its potential in treating various diseases, thereby contributing to advancements in medical treatment options.

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

• 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 
• 118895-95-7 2-desamino-5,8-dideazaisofolic acid 
• 118895-90-2 di-tert-butyl 2-desamino-5,8-dideazaisofolate 
• 1036390-09-6 C₁₈H₁₇N₃O₅ 

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.

Method for synthesizing lapatinib or intermediate 5-(4-hydroxy quinazoline)-furan-2-formaldehyde of lapatinib

The invention relates to a method for synthesizing lapatinib or intermediate 5-(4-hydroxy quinazoline)-furan-2-formaldehyde of lapatinib. The method for synthesizing the intermediate comprises steps as follows: 4-hydroxy-6-nitro quinazoline reacts with hydrazine hydrate in a solvent in the presence of a catalytic amount of catalyst, and 4-hydroxy-6-amino quinazoline is prepared; 4-hydroxy-6-amino quinazoline reacts with furaldehyde in the solvent in presence of acid, sodium nitrite and a catalytic amount of catalyst, and the intermediate is prepared. The invention further relates to a method for synthesizing lapatinib and/or a lapatinib salt, a lapatinib intermediate and/or a pharmaceutically acceptable salt of the intermediate. The method is performed by using the intermediate synthesized with the method. The method has the advantages that steps are simplified, agents are cheap, available and high in utilization rate, heavy metal pollution is avoided, the reaction condition/operation requirement is lower and/or the yield is high and the like.

Design and synthesis of novel quinazoline derivatives and their evaluation as PI3Ks inhibitors

The aim of this work was to synthesize 4-acetamido-, 4-amino- and 4-oxo-6-substituted aminoquinazolines and to evaluate them as phosphoinositide 3-kinases (PI3Ks) inhibitors. The respective chemotype was designed based on combining the structural features

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.

Substituted 2H-isoquinolin-1-one as potent Rho-Kinase inhibitors. Part 1: Hit-to-lead account

Two closely related scaffolds were identified through an uHTS campaign as desirable starting points for the development of Rho-Kinase (ROCK) inhibitors. Here, we describe our hit-to-lead evaluation process which culminated in the rapid discovery of potent leads such as 22 which successfully demonstrated an early in vivo proof of concept for anti-hypertensive activity.

BICYCLIC LACTAM FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention provides novel bicyclic lactams derivatives, and analogues thereof, of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables A, B, C, W, Y, Z1, Z2, Z3, Z4, R8, and R9 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.

MACROCYCLIC FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention relates generally to novel macrocycles of Formula (I) or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein the variables A, B, C, D, L, M, W, Z1, Z2, Z3, Z4, R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.

SUBSTITUTED ARYL-AMINE DERIVATIVES AND METHODS OF USE

The present invention provides classes of compounds, including-their pharmaceutically acceptable derivatives, useful for treating angiogenesis and related diseases such as cancer. Formula I and II wherein R is a 9- or 10-membered heterocyclyl ring selected from 7-isoquinolinyl,..2-methyl-3-oxo-2,3-dihydroindazol-6-yl, [1,6]-naphthydrin-3-yl, [1,7]-naphthydrin-2-yl, 1-oxo-2,3-dihydrobenzofuran-4-yl, 3-oxo-2,3-dihydrobenzofuran-5-yl, dihydro-benzodioxinyl, 6-quinazolinyl, 2-amino-6-quinazolinyl, 4-methylamino-6-quinazolinyl, 2,4-diamino-6 quinazolinyl, 3-oxo-3,4-dihydro-1,4-benzoxazin-6-yl, 2,2-difluoro-l;3-benzodioxol-5-yl and 2,2,3,3 tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-yl, each of which is optionally substituted with one or more substituents selected from halo, haloakyl, C1-6 alkyl, C2-8 alkenyl, C2-8 alkynyl, N-dimethylamino-C1-6-alkyl, N-dimethylamino-C1-6-alkoxy, amino, alkyl-carbonylamino, morpholino-sulfonyl, amino-sulfonyl, oxazolyl, pyrrolyl,4 morpholinyl, carboxyl, cyano, and acetyl; wherein R1 in formula I is selected from unsubstituted or substituted phenyl, 5-6 membered heteroaryl, 9-10 membered bicyclic heterocyclyl and 11-14 membered tricyclic heterocyclyl, and R1 in formula II is selected from specific bicyclic heterocycles.

Efficient synthesis of thiazoloquinazolinone derivatives

An original route to the rare 8H-thiazolo[5,4-f]quinazolin-9-one 1 and the novel 7H-thiazolo[4,5-h]quinazolin-6-one 2 is described. Access to the regioisomers was realized by fusion of a thiazole and a quinazoline ring via Appel's salt chemistry. Thermal