| Identification | More | [Name]
4-Hydroxyquinazoline | [CAS]
491-36-1 | [Synonyms]
4-(1H)-QUINAZOLINONE
4(3H)-QUINAZOLINONE
4-HQN
4-HYDROXYQUINAZOLINE
4-QUINAZOLINO
4-QUINAZOLINOL
4-QUINAZOLONE
AKOS 219-06
AKOS BBS-00002691
AURORA 17795
quinazolidin-4-one
QUINAZOLIN-4(3H)-ONE
QUINAZOLIN-4-OL
QUINAZOLONE
TIMTEC-BB SBB005858
4(3H)-Quinazolone
4-Oxoquinazoline
4-Quinazolinone
Quinazolone, 4-
quinazolin-4(1H)-one | [EINECS(EC#)]
207-735-8 | [Molecular Formula]
C8H6N2O | [MDL Number]
MFCD00511302 | [Molecular Weight]
146.15 | [MOL File]
491-36-1.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light beige crystalline powder | [Melting point ]
216-219 °C (lit.) | [Boiling point ]
265.75°C (rough estimate) | [density ]
1.2312 (rough estimate) | [vapor pressure ]
0.015Pa@20°C | [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 Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [RTECS ]
VA2300000
| [HazardClass ]
IRRITANT | [HS Code ]
29335995 |
| Hazard Information | Back Directory | [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]
Notclassified(100%) | [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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