4-Hydroxyquinazoline Chemical Properties

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)

Safety Information

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

MSDS

• Language:English Provider:4-Hydroxyquinazoline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Hydroxyquinazoline Usage And Synthesis

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

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