206257-39-8

Basic information

• Product Name: ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE
• Synonyms: ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE;6-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;UKRORGSYN-BB BBV-080772;6-Bromo-4-chloro-3-quinolinecarboxylic acid ethyl ester;ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE-4;EOS-60328;3-Quinolinecarboxylic acid, 6-bromo-4-chloro-, ethyl ester
• CAS NO: 206257-39-8
• Molecular Formula: C₁₂H₉BrClNO₂
• Molecular Weight: 314.56
• EINECS: 1592732-453-0
• Mol File: 206257-39-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: 100-102°
• Boiling Point: 378.3°C at 760 mmHg
• Flash Point: 182.6°C
• Appearance: /
• Density: 1.578
• Vapor Pressure: 6.33E-06mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.98±0.27(Predicted)
• Water Solubility: Immiscible in water.
• CAS DataBase Reference: ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE(206257-39-8)
• EPA Substance Registry System: ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE(206257-39-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 206257-39-8(Hazardous Substances Data)

Usage

Uses

Ethyl 6-bromo-4-chloroquinoline-3-carboxylate is used as pharmaceutical intermediates

InChI:InChI=1/C12H9BrClNO2/c1-2-17-12(16)9-6-15-10-4-3-7(13)5-8(10)11(9)14/h3-6H,2H2,1H3

Upstream product

• 122794-99-4 6-bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 106-40-1 4-bromo-aniline 
• 101937-44-4 diethyl 2-((4-bromophenylamino)methylene)malonate 
• 79607-23-1 ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate 
• 1248546-11-3 ethyl 6-bromo-1-[(4-methoxyphenyl)methyl]-4-oxoquinoline-3-carboxylate 
• 1117-37-9 ethyl (E)-3-(dimethylamino)acrylate 
• 773140-42-4 2-bromo-5-fluorobenzoyl chloride 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 146328-85-0 5-bromo-2-fluoro-benzoic acid 

Downstream Products

• 206257-98-9 4-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-6-bromo-quinoline-3-carboxylic Acid Ethyl Ester 
• 206258-03-9 4-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-6-bromo-quinoline-3-carboxylic Acid 
• 449197-37-9 6-bromo-4-(4-methoxyphenylamino)-quinoline-3-carboxylic acid ethyl ester 
• 449196-96-7 6-bromo-4-p-tolyl-amino-quinoline-3-carboxylic acid ethyl ester 
• 449196-93-4 ethyl 6-bromo-4-(phenylamino)quinoline-3-carboxylate 
• 1215525-57-7 8-bromo-1,2-dihydro-2-phenyl-3H-pyrazolo[4,3-c]quinolin-3-one 
• 1207282-77-6 8-bromo-2-(4-fluoroyphenyl)-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 1207282-79-8 1-benzyl-7,9-dichloro-1H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 1207282-76-5 2-benzyl-7,9-dichloro-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 1207282-78-7 2-benzyl-8-bromo-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 1207282-80-1 1-benzyl-8-bromo-1,2-dihydro-3H-pyrazolo[4,3-c]quinolin-3(2H)-one 
• 449197-18-6 ethyl 6-bromo-4-(4-fluorophenylamino)-quinoline-3-carboxylate 
• 449197-16-4 ethyl 6-bromo-4-(4-chlorophenylamino)-quinoline-3-carboxylate 
• 1256468-41-3 ethyl 6-bromo-4-[(4-isopropylphenyl)-amino]quinoline-3-carboxylate 

Relevant articles and documents

Discovery and Mechanistic Study of Tailor-Made Quinoline Derivatives as Topoisomerase 1 Poison with Potent Anticancer Activity

To overcome chemical limitations of camptothecin (CPT), we report design, synthesis, and validation of a quinoline-based novel class of topoisomerase 1 (Top1) inhibitors and establish that compound 28 (N-(3-(1H-imidazol-1-yl)propyl)-6-(4-methoxyphenyl)-3-(1,3,4-oxadiazol-2-yl)quinolin-4-amine) exhibits the highest potency in inhibiting human Top1 activity with an IC50 value of 29 ± 0.04 nM. Compound 28 traps Top1-DNA cleavage complexes (Top1ccs) both in the in vitro cleavage assays and in live cells. Point mutation of Top1-N722S fails to trap compound 28-induced Top1cc because of its inability to form a hydrogen bond with compound 28. Unlike CPT, compound 28 shows excellent plasma serum stability and is not a substrate of P-glycoprotein 1 (permeability glycoprotein) advancing its potential anticancer activity. Finally, we provide evidence that compound 28 overcomes the chemical instability of CPT in human breast adenocarcinoma cells through generation of persistent and less reversible Top1cc-induced DNA double-strand breaks as detected by γH2AX foci immunostaining after 5 h of drug removal.

BICYCLIC HETEROCYCLIC COMPOUNDS USEFUL AS IRAK4 INHIBITORS

Disclosed are compounds of Formula (I) or a salt or prodrug thereof, wherein: X is CR4a4a or N; Y is CR4b4b or N; Z is CR4d4d or N; provided that zero or 1 of X, Y, and Z is N; and R11, R22, R33, R4a4a, R4b4b, R4c4c, and R4d4d are define herein. Also disclosed are methods of using such compounds as modulators of IRAK4, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases, or in the treatment of cancer.

Synthesis and biological evaluation of small molecule modulators of CDK8/Cyclin C complex with phenylaminoquinoline scaffold

Background. CDK8/CycC complex has kinase activity towards the carboxyterminal domain of RNA polymerase II, and contributes to the regulation of transcription via association with the mediator complex. Different human malignancies, mainly colorectal and gastric cancers, were produced as a result of overexpression of CDK8/CycC in the mediator complex. Therefore, CDK8/CycC complex represents as a cancer oncogene and it has become a potential target for developing CDK8/CycC modulators. Methods. A series of nine 4-phenylaminoquinoline scaffold-based compounds 5a-i was synthesized, and biologically evaluated as potential CDK8/CycC complex inhibitors. Results. The scaffold substituent effects on the intrinsic inhibitory activity toward CDK8/CycC complex are addressed trying to present a novel outlook of CDK8/CycC Complex inhibitors with 4-phenylaminoquinoline scaffold in cancer therapy. The secondary benzenesulfonamide analogues proved to be the most potent compounds in suppressing CDK8/CycC enzyme, whereas, their primary benzenesulfonamide analogues showed inferior activity. Moreover, the benzene reversed sulfonamide analogues were totally inactive. Discussion. The titled scaffold showed promising inhibitory activity data and there is a crucial role of un/substituted sulfonamido group for CDK8/CycC complex inhibitory activity. Compound 5d showed submicromolar potency against CDK8/CycC (IC50 = 0.639 μM) and it can be used for further investigations and to design another larger library of phenylaminoquinoline scaffold-based analogues in order to establish detailed SARs.

PAPD5 INHIBITORS AND METHODS OF USE THEREOF

The present application provides compounds that are PAPD5 inhibitors and are useful in treating a variety of conditions such as cancer, telomere diseases, and aging-related and other degenerative disorders.