150449-97-1

Basic information

• Product Name: 4-Chloroquinazoline-6-carbonitrile
• Synonyms: 4-Chloroquinazoline-6-carbonitrile;4-CHLOROQUINAZOLINE-6-CARBONIT;4-chloro-6-Quinazolinecarbonitrile
• CAS NO: 150449-97-1
• Molecular Formula: C₉H₄ClN₃
• Molecular Weight: 189.605
• Mol File: 150449-97-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 368.464 °C at 760 mmHg
• Flash Point: 176.641 °C
• Appearance: /
• Density: 1.444 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.675
• PKA: 0.06±0.50(Predicted)
• CAS DataBase Reference: 4-Chloroquinazoline-6-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloroquinazoline-6-carbonitrile(150449-97-1)
• EPA Substance Registry System: 4-Chloroquinazoline-6-carbonitrile(150449-97-1)

Safety Data

• Hazardous Substances Data: 150449-97-1(Hazardous Substances Data)

Usage

Uses

4-Chloroquinazoline-6-carbonitrile is a useful reactant for the synthesis and preparation of quinazoline based inhibitors of IRAK4, which are used to treat inflammation.

InChI:InChI=1/C9H4ClN3/c10-9-7-3-6(4-11)1-2-8(7)12-5-13-9/h1-3,5H

Upstream product

• 32084-59-6 6-bromo-4-hydroxyquinazoline 
• 84166-88-1 4-aminoisophthalamide 
• 150454-06-1 6-carbamoylquinazolin-4(3H)-one 

Downstream Products

• 1820787-94-7 4-{[trans-4-(morpholin-4-yl)cyclohexyl]amino}quinazoline-6-carbonitrile 
• 1202227-42-6 C₁₅H₉ClN₄ 
• 773884-30-3 4-(Benzylamino)quinazoline-6-carbonitrile 

Relevant articles and documents

COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE 4 POLYPEPTIDES

The present disclosure relates to bifunctional compounds, which find utility as modulators of Interleukin-1 Receptor-Associated Kinase 4 (IRAK-4); the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hppel-Lindau, cereblon, ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

Method of treating a patient having a precancerous lesions with amide quinazoline derivatives

Derivatives of quinazoline are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit the growth of neoplastic cells.

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.