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HomeProduct name list4-Hydroxyquinazoline

4-Hydroxyquinazoline

Synonym(s):4-Quinazolinol

  • CAS NO.:491-36-1
  • Empirical Formula: C8H6N2O
  • Molecular Weight: 146.15
  • MDL number: MFCD00511302
  • EINECS: 207-735-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
4-Hydroxyquinazoline Structural

What is 4-Hydroxyquinazoline?

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

The Uses of 4-Hydroxyquinazoline

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

The Uses of 4-Hydroxyquinazoline

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.

What are the applications of Application

4-HQN is a potent and selective PARP-1, NFkB activation, and AP-1 inhibitor

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

Properties of 4-Hydroxyquinazoline

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.
CAS DataBase Reference 491-36-1(CAS DataBase Reference)
NIST Chemistry Reference 4(1H)-quinazolinone(491-36-1)

Safety information for 4-Hydroxyquinazoline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral

Computed Descriptors for 4-Hydroxyquinazoline

InChIKey QMNUDYFKZYBWQX-UHFFFAOYSA-N

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