4-Hydroxyquinazoline Basic information

Product Name:

4-Hydroxyquinazoline

Synonyms:

4(3H)-Quinazolone;4-Oxoquinazoline;4-Quinazolinone;Quinazolone, 4-;quinazolidin-4-one;1H-quinazolin-4-one;4-HydroxyquinazoL;Quinazolin-4-ol, 4-Quinazolinol

CAS:

491-36-1

MF:

C8H6N2O

MW:

146.15

EINECS:

207-735-8

Product Categories:

Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;H;Heterocyclic Building Blocks;PYRIMIDINE;Alcohols and Derivatives;Heterocycles;Quinolines, Quinazolines and derivatives;quinazolinone;Caspases/Apoptosis;Quinazolines

Mol File:

491-36-1.mol

4-Hydroxyquinazoline Chemical Properties

Melting point 

216-219 °C (lit.)

Boiling point 

265.75°C (rough estimate)

density 

1.2312 (rough estimate)

refractive index 

1.4900 (estimate)

storage temp. 

Sealed in dry,Room Temperature

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

InChIKey

QMNUDYFKZYBWQX-UHFFFAOYSA-N

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

4-Hydroxyquinazoline Usage And Synthesis

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.

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.

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.