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| 4-Hydroxyquinazoline Basic information |
| 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) |
| 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 shows anti-microbial and anti-carcinogenic activity as seen in studies due to the quinazoline moiety. | | 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. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 16, p. 1669, 1951 DOI: 10.1021/jo50005a003 | | Flammability and Explosibility | Notclassified | | 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 |
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