ChemicalBook > CAS DataBase List > 4-Hydroxyquinazoline

4-Hydroxyquinazoline

Product Name
4-Hydroxyquinazoline
CAS No.
491-36-1
Chemical Name
4-Hydroxyquinazoline
Synonyms
QUINAZOLIN-4(3H)-ONE;QUINAZOLINONE;4-Oxoquinazoline;QUINAZOLIN-4-OL;quinazolin-4(1H)-one;QUINAZOLONE;4-HQN;β-Nitropropionic acid;AKOS 219-06;AURORA 17795
CBNumber
CB5182082
Molecular Formula
C8H6N2O
Formula Weight
146.15
MOL File
491-36-1.mol
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4-Hydroxyquinazoline Property

Melting point:
216-219 °C (lit.)
Boiling point:
265.75°C (rough estimate)
Density 
1.2312 (rough estimate)
vapor pressure 
0.015Pa at 20℃
refractive index 
1.4900 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Soluble in DMSO (up to 14 mg/ml) or in Water (up to 1 mg/ml).
form 
Crystalline Powder
pka
2.69±0.20(Predicted)
color 
Off-white to light beige
Water Solubility 
Soluble in DMSO (100 mM), ethanol, methanol, and water (10 mM).
Sensitive 
Hygroscopic
BRN 
118473
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month.
InChIKey
QMNUDYFKZYBWQX-UHFFFAOYSA-N
LogP
0.94 at 20℃
CAS DataBase Reference
491-36-1(CAS DataBase Reference)
NIST Chemistry Reference
4(1H)-quinazolinone(491-36-1)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-22
Safety Statements 
26-37/39-36/37/39-22
WGK Germany 
3
RTECS 
VA2300000
HazardClass 
IRRITANT
HS Code 
29335995
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H57807
Product name
4-Hydroxyquinazoline
Purity
98%
Packaging
5g
Price
$26.22
Updated
2024/03/01
TCI Chemical
Product number
H0803
Product name
4-Hydroxyquinazoline
Purity
>98.0%(T)
Packaging
5g
Price
$16
Updated
2024/03/01
TCI Chemical
Product number
H0803
Product name
4-Hydroxyquinazoline
Purity
>98.0%(T)
Packaging
25g
Price
$39
Updated
2024/03/01
Alfa Aesar
Product number
A17129
Product name
4-Hydroxyquinazoline, 98%
Packaging
10g
Price
$36.65
Updated
2024/03/01
Alfa Aesar
Product number
A17129
Product name
4-Hydroxyquinazoline, 98%
Packaging
50g
Price
$107.65
Updated
2024/03/01
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4-Hydroxyquinazoline Chemical Properties,Usage,Production

Description

4-HQN (491-36-1) is an inhibitor of poly(ADP-ribose) polymerase (PARP) (IC50?= 9.5 μM).1?Displays mixed inhibition with respect to NAD+. Protective against ischemia-reperfusion induced ROS production, and subsequent mitochondrial and cell damage in rat heart.2?4-HQN is anti-inflammatory in LPS-induced endotoxic mice?in vivo; decreases NF-κB and AP-1 activation.3

Chemical Properties

off-white to light beige crystalline powder

Uses

4-Hydroxyquinazoline is been used to inhibit PARP (poly(ADP-ribose) synthetase) which catalyzes covalent attachment of the ADP-ribose moiety of NAD+ to various proteins. This compound specifically and potently inhibits PARP-1. 4-HQN demonstrates the ability to decrease activation of transcription factor NFκB and AP-1 in lipopolysaccharide-induced shock. Mechanistic studies indicate that 4-HQN activates PI3-kinase/Akt pathway in the liver, spleen, and lung and down-regulates two elements of the MAP kinase system. Additionally, this agent has been observed to decrease ischemia-reperfusion-induced increase of protein oxidation, single-strand DNA breaks, lipid peroxidation, and mitochondrial reactive oxygen species production in the reperfusion period.

Uses

4-Hydroxyquinazoline shows anti-microbial and anti-carcinogenic activity as seen in studies due to the quinazoline moiety.

Definition

ChEBI: 1H-quinazolin-4-one is a member of quinazolines.

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 1669, 1951 DOI: 10.1021/jo50005a003

Flammability and Explosibility

Not classified

Biological Activity

Inhibitor of poly(ADP-ribose) polymerase (PARP) (IC 50 = 9.5 μ M); displays mixed inhibition with respect to NAD + . Protective against ischemia-reperfusion induced ROS production, and subsequent mitochondrial and cell damage in rat heart. Anti-inflammatory in LPS-induced endotoxic mice in vivo ; decreases NF- κ B and AP-1 activation.

References

1) Banasil?et al. (1992),?Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase;? J. Biol. Chem.,?267?1569 2) Halmosi?et al. (2001),?Effect of poly(ADP-ribose) polymerase inhibitors on the ischemia-reperfusion-induced oxidative cell damage and mitochondrial metabolism in Langendorff heart perfusion system.? Clin. Mol. Pharmacol.,?59?1497 3) Veres?et al. (2004),?Regulation of kinase cascades and transcription factors by a poly(ADP-ribose) polymerase-1 inhibitor, 4-hydroxyquinazoline, in lipopolysaccharide-induced inflammation in mice;? J. Pharmacol. Exp. Ther.,?310?247

4-Hydroxyquinazoline Preparation Products And Raw materials

Raw materials

Four-necked flask Stainless steel reaction pot 2-Quinoxalinone Light red Anthranilic acid

Preparation Products

4-Chloroquinazoline
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4-Hydroxyquinazoline Suppliers

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View Lastest Price from 4-Hydroxyquinazoline manufacturers

Henan Fengda Chemical Co., Ltd
Product
4-Hydroxyquinazoline 491-36-1
Price
US $8.00-0.80/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-09
Hebei Zhanyao Biotechnology Co. Ltd
Product
4-Hydroxyquinazoline 491-36-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 Tons
Release date
2021-10-13
Career Henan Chemical Co
Product
4-Hydroxyquinazoline 491-36-1
Price
US $3.00/KG
Min. Order
1KG
Purity
90%-99.9%
Supply Ability
500kg
Release date
2019-07-04

491-36-1, 4-HydroxyquinazolineRelated Search:

Triadimefon Quinocetone Trazodone Quinazoline Cefazolin 2-Quinolinol 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one 2-Quinoxalinone Sulfaquinoxaline Furazolidone Gliquidone Cefazolin sodium salt 2-(TRICHLOROMETHYL)QUINAZOLIN-4(3H)-ONE 7-NITRO-3H-QUINAZOLIN-4-ONE mecloqualone 3-PHENYL-4-[3H]QUINAZOLINONE METHAQUALONE 2-MERCAPTO-4(3H)-QUINAZOLINONE

  • 4(3H)-Quinazolone
  • 4-Oxoquinazoline
  • 4-Quinazolinone
  • Quinazolone, 4-
  • quinazolidin-4-one
  • 1H-quinazolin-4-one
  • 4-HydroxyquinazoL
  • Quinazolin-4-ol, 4-Quinazolinol
  • QUINAZOLIN-4(3H)-ONE
  • QUINAZOLIN-4-OL
  • QUINAZOLONE
  • TIMTEC-BB SBB005858
  • AURORA 17795
  • 4-HQN
  • 4-HYDROXYQUINAZOLINE
  • 4-QUINAZOLINO
  • 4-QUINAZOLINOL
  • 4-QUINAZOLONE
  • 4-(1H)-QUINAZOLINONE
  • 4(3H)-QUINAZOLINONE
  • AKOS 219-06
  • AKOS BBS-00002691
  • quinazolin-4(1H)-one
  • 3,4-Dihydroquinazolin-4-One
  • 4-Hydroxyquizoline
  • QUINAZOLINONE
  • 3H-QUINAZOLIN-4-ONE
  • 4(1H)-Quinazolinone (6CI,7CI,8CI,9CI)
  • 4-Hydroxyquinazoline,98%
  • 4-Hydroxyquinazoline for synthesis
  • 4-Hydroxyquinazoline, 98% 5GR
  • quinazoline-4(3H)-one
  • JACS-491-36-1
  • 4-Hydroxyquinazoline&gt
  • 4-Hydroxyquinazoline ISO 9001：2015 REACH
  • Chinazolin-4(1H)-on
  • β-Nitropropionic acid
  • Phenol,2,2'-[1,7-ethanediylbis(iminomethylene)]bis-
  • 2-Naphthalenecarboxylicacid,10-amino-,methylester
  • 491-36-1
  • ALCOHOL
  • Quinazolines
  • Heterocyclic Building Blocks
  • Building Blocks
  • Bioactive Small Molecules
  • Building Blocks
  • Cell Biology
  • Chemical Synthesis
  • H
  • Heterocyclic Building Blocks
  • Quinazolines
  • Caspases/Apoptosis
  • quinazolinone
  • Quinolines, Quinazolines and derivatives
  • Alcohols and Derivatives
  • Heterocycles
  • PYRIMIDINE