154288-09-2

Basic information

• Product Name: 4-Chloro-8-methoxyquinazoline
• Synonyms: 4-Chloro-8-methoxyquinazoline; quinazoline, 4-chloro-8-methoxy-
• CAS NO: 154288-09-2
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• Mol File: 154288-09-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 322.973°C at 760 mmHg
• Flash Point: 149.129°C
• Appearance: /
• Density: 1.333g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.42±0.30(Predicted)
• CAS DataBase Reference: 4-Chloro-8-methoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-8-methoxyquinazoline(154288-09-2)
• EPA Substance Registry System: 4-Chloro-8-methoxyquinazoline(154288-09-2)

Safety Data

• Hazardous Substances Data: 154288-09-2(Hazardous Substances Data)

Usage

Uses

4-Chloro-8-methoxyquinazoline is used in preparation of of Quinazoline derivatives as Ectonucleotide Pyrophosphatase Phosphodiesterase 1 inhibitors.

InChI:InChI=1/C9H7ClN2O/c1-13-7-4-2-3-6-8(7)11-5-12-9(6)10/h2-5H,1H3

Upstream product

• 5121-34-6 methyl 2-amino-3-methoxybenzoate 
• 16064-27-0 8-methoxy-quinazolin-4(3H)-one 

Downstream Products

• 154288-08-1 4-chloroquinazolin-8-ol 
• 1112986-02-3 4-chloro-3-[8-methoxyquinazolin-4-yl]-phenol 
• 101284-88-2 benzyl-(8-methoxy-quinazolin-4-yl)-amine 

Relevant articles and documents

Small-molecule phosphodiesterase probes: Discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

PDE1 is a family of calcium-activated, dual substrate phosphodiesterases expressed in both the CNS and periphery that play a role in the integration of intracellular calcium and cyclic nucleotide signaling cascades. Exploration of the potential in targeting this family of enzymes to treat neuropsychiatric disorders has been hampered by a lack of potent, selective, and brain penetrable PDE1 inhibitors. To identify such compounds we used high-throughput screening, structure-based design, and targeted synthetic chemistry to discover the 4-aminoquinazoline 7a (PF-04471141) and the 4-indanylquinazoline 27 (PF-04822163) each of which are PDE1 inhibitors that readily cross the blood brain barrier. These quinazoline-based PDE1-selective inhibitors represent valuable new tools to study the biological processes regulated by PDE1 and to begin to determine the potential therapeutic utility of such compounds to treat neuropsychiatric disorders.

CHEMICAL COMPOUNDS

The invention relates to chemical compounds of the formula (I) or pharmaceutically acceptable salts thereof, which possess B Raf inhibitory activity and are accordingly useful for their anti cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use in the production of an anti-cancer effect in a warm blooded animal such as man.

Cyclic GMP Phosphodiesterase Inhibitors. 2. Requirement of 6-Substitution of Quinazoline Derivatives for Potent and Selective Inhibitory Activity

We synthesized various 4-amino>quinazolines substituted at the 5- to 8-positions and evaluated their inhibitory activities toward cyclic GMP phosphodiesterase (cGMP-PDE) from porcine aorta.Monosubstitution at the 6-position was essential for the inhibitory activity, and the preferred substituents were compact and hydrophobic: methoxy (3b, IC50 = 0.23 μM), methyl (3c, 0.10 μM), chloro (3d, 0.019 μM), thiomethyl (3f, 0.031 μM), and cyano (3p, 0.090 μM) groups.Compounds 3b-d, f, p lacked inhibitory activity toward other PDE isozymes (all IC50 values > 100 μM), and their relaxing activities in porcine coronary arteries were well correlated with the inhibitory activities toward cGMP-PDE (r = 0.88, p 0.05).One of these compounds, 3b, elevated the intracellular cGMP level in isolated porcine coronary arteries without causing any change in the cAMP level.We consider that this series of compounds dilates coronary arteries via potent and specific inhibition of cGMP-PDE.