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
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) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Computed Descriptors for 4-Hydroxyquinazoline
InChIKey | QMNUDYFKZYBWQX-UHFFFAOYSA-N |
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