263149-10-6

Basic information

• Product Name: 4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE
• Synonyms: 4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE;4-Chloro-3-cyano-7-hydroxy-6-methoxyquinoline;4-Chloro-7-hydroxy-6-methoxy-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 4-chloro-7-hydroxy-6-Methoxy-
• CAS NO: 263149-10-6
• Molecular Formula: C₁₁H₇ClN₂O₂
• Molecular Weight: 234.63848
• EINECS: 1592732-453-0
• Mol File: 263149-10-6.mol

Chemical Properties

• Boiling Point: 438.954 °C at 760 mmHg
• Flash Point: 219.272 °C
• Appearance: /
• Density: 1.48
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.41±0.40(Predicted)
• CAS DataBase Reference: 4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE(263149-10-6)
• EPA Substance Registry System: 4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE(263149-10-6)

Safety Data

• Hazardous Substances Data: 263149-10-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-hydroxy-6-methoxy-quinoline-3-carbonitrile is used as a key intermediate in the synthesis of Src inhibitors for the development of drugs targeting various diseases. Src inhibitors are of interest due to their potential role in treating conditions such as cancer, where they can help regulate cell growth and division, as well as other cellular processes.
Used in Chemical Research:
4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE is also utilized in chemical research for the exploration of novel quinoline-based structures and their potential applications. The presence of functional groups in 4-chloro-7-hydroxy-6-methoxy-quinoline-3-carbonitrile allows for further chemical modifications and the development of new derivatives with improved properties and therapeutic effects.

InChI:InChI=1/C11H7ClN2O2/c1-16-10-2-7-8(3-9(10)15)14-5-6(4-13)11(7)12/h2-3,5,15H,1H3

Upstream product

• 741276-43-7 7-isopropyloxy-6-methoxy-4-chloroquinoline-3-carbonitrile 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 3535-27-1 methyl 4-isopropoxy-3-methoxybenzoate 
• 214476-99-0 7-benzyloxy-4-chloro-6-methoxyquinoline-3-carbonitrile 
• 319492-96-1 7-isopropyloxy-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile 
• 948553-02-4 4-isopropoxy-5-methoxy-2-nitro-benzoic acid methyl ester 
• 50413-53-1 methyl 2-amino-4-isopropoxy-5-methoxybenzoate 

Downstream Products

• 214470-68-5 7-(3-chloro-propoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile 
• 380844-38-2 4-chloro-7-(4-chlorobutoxy)-6-methoxy-3-quinolinecarbonitrile 
• 380844-40-6 4-chloro-7-(5-chloropentoxy)-6-methoxy-3-quinolinecarbonitrile 
• 214470-72-1 4-chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrile 
• 423180-28-3 4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile 
• 622369-44-2 4-chloro-6-methoxy-7-(2-methoxy-ethoxy)-quinoline-3-carbonitrile 
• 214487-30-6 (4-chloro-6-methoxy-7-[3-(1-morpholino)propoxy]-3-quinolinecarbonitrile) 
• 492444-39-0 7-[3-(4-methylpiperazin-1-yl)propoxy]-6-methoxy-4-chloro-quinoline-3-carbonitrile 
• 214470-55-0 4-chloro-6,7-dimethoxyquinoline-3-carbonitrile 
• 622368-88-1 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]-3-quinolinecarbonitrile 
• 622369-21-5 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile 
• 380844-42-8 7-(2-chloroethoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile 
• 380844-44-0 7-(4-chlorobutoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile 

Relevant articles and documents

Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors

This invention provides compounds of formula 1 wherein R1, G1, G2, R4, Z, X and n are defined herein, or a pharmaceutically acceptable salt thereof, which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

The design, synthesis and biological evaluation of 7-alkoxy-4-heteroarylamino-3-cyanoquinolines as dual inhibitors of c-Src and iNOS

Because both c-Src and iNOS are key regulatory enzymes in tumorigenesis, a new series of 4-heterocycle amine-3-quinolinecarbonitriles as potent dual inhibitors of both enzymes were designed, synthesized and evaluated as multiple targets agents in cancer therapy. All compounds were evaluated by two related enzyme inhibition assays and an anti-proliferation assay in vitro. The results showed that most compounds inhibited c-Src and iNOS well. The best compound 8 inhibited both enzymes with the IC50 values of 34.8 nM and 26.7 μM. Several compounds also showed moderate anti-proliferation at 10 μM against colon and liver cancer cell lines.

Derivatives of quinoline as inhibitors for MEK

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof. wherein: n is 0-1; X and Y are independently selected from -NH-, -O-, -S-, or -NR8- where R8 is alkyl of 1-6 carbon atoms and X may additionally comprise a CH2 group; R7 is a group (CH2)mR9 where m is 0,or an integer of from 1-3 and R9 is a substituted aryl group, an optionally substituted cycloalkyl ring of up to 10 carbon atoms, or an optionally substituted heterocyclic ring or an N-oxide of any nitrogen containing ring; R6 is a divalent cycloalkyl of 3 to 7 carbon atoms, which may be optionally further substituted with one or more alkyl of 1 to 6 carbon atom groups; or is a divalent pyridinyl, pyimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally further substituted with one or more specified groups; R1, R2, R3 and R4 are each independently selected from hydrogen or various specified organic groups. Compounds are useful as pharmaceuticals for the inhibition of MEK activity.

SUBSTITUTED 3-CYANOQUINOLINES AS PROTEIN TYROSINE KINASES INHIBITORS

This invention provides compounds of formula (1) wherein R1, G1, G2, R4, Z, X and n are defined herein, or a pharmaceutically acceptable salt thereof, which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

Substituted 3-cyanoquinolines

This invention provides compounds of formula I having the structure wherein G1, G2, R1, R4, Z, n, and X are defined in the specification or a pharmaceutically acceptable salt thereof which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

Inhibitors of Src tyrosine kinase: The preparation and structure-activity relationship of 4-anilino-3-cyanoquinolines and 4-anilinoquinazolines

Src is a nonreceptor tyrosine kinase involved in signaling pathways that control proliferation, migration, and angiogenesis. Increased Src expression and activity are associated with an increase in tumor malignancy and poor prognosis. Several quinolines and quinazolines were identified as potent and selective inhibitors of Src kinase activity. (C) 2000 Elsevier Science Ltd.