79607-23-1

Basic information

• Product Name: ethyl 6-broMo-4-oxo-1,4-dihydroquinoline-3-carboxylate
• Synonyms: ethyl 6-broMo-4-oxo-1,4-dihydroquinoline-3-carboxylate;6-BroMo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester;ethyl 6-broMo-4-oxo-1,4-dihydroquinoline-3-carboxylate-3;3-Quinolinecarboxylic acid, 6-bromo-1,4-dihydro-4-oxo-, ethyl ester
• CAS NO: 79607-23-1
• Molecular Formula: C₁₂H₁₀BrNO₃
• Molecular Weight: 296.1167
• Mol File: 79607-23-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 326-329℃
• Boiling Point: 394.4°C at 760 mmHg
• Flash Point: 192.3°C
• Appearance: /
• Density: 1.555g/cm³
• Vapor Pressure: 1.98E-06mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.24±0.70(Predicted)
• CAS DataBase Reference: ethyl 6-broMo-4-oxo-1,4-dihydroquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 6-broMo-4-oxo-1,4-dihydroquinoline-3-carboxylate(79607-23-1)
• EPA Substance Registry System: ethyl 6-broMo-4-oxo-1,4-dihydroquinoline-3-carboxylate(79607-23-1)

Safety Data

• Hazard Codes: Xi:
• Hazardous Substances Data: 79607-23-1(Hazardous Substances Data)

Usage

General Description

Ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate is a specialized organic compound that belongs to the chemical class of quinolines, which are aromatic compounds containing a two fused six- and five-member aromatic rings. Its molecular structure consists of a 1,4-dihydroquinoline ring, which is modified with a bromine atom at the 6th position, a carboxylate group at the 3rd position, and an ethyl ester functional group. This chemical is often used in pharmaceutical industry and in various chemical reactions as an intermediate. Like other quinolines, the compound's properties can vary greatly depending on its specific structure and the presence of other functional groups. These properties can include stability, reactivity, and various physical characteristics like melting point and solubility.

InChI:InChI=1/C12H10BrNO3/c1-2-17-12(16)9-6-14-10-4-3-7(13)5-8(10)11(9)15/h3-6H,2H2,1H3,(H,14,15)

Upstream product

• 101937-44-4 diethyl 2-((4-bromophenylamino)methylene)malonate 
• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 106-40-1 4-bromo-aniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 224175-70-6 ethyl 6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-quinolone-3-carboxylate 
• 145369-94-4 6-bromo-3-quinolinecarboxylic acid-4-ol 
• 65340-70-7 6-bromo-4-chloroquinoline 
• 206257-39-8 6-bromo-4-chloroquinoline-3-carboxylic acid ethyl ester 
• 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 

Relevant articles and documents

Quinolone-N-acylhydrazone hybrids as potent Zika and Chikungunya virus inhibitors

This work reports the synthesis of quinolone-N-acylhydrazone hybrids, namely 6-R-N'-(2-hydxoxybenzylidene)-4-oxo-1,4-dihydroquinoline-3-carbohydrazide (R = H: 5a, F: 5b, Cl: 5c and Br: 5d), which exhibited excellent activity against arbovirus Zika (ZIKV) and Chikungunya (CHIKV). In vitro screening towards ZIKV and CHIKV inhibition revealed that all substances have significant antiviral activity, most of them being more potent than standard Ribavirin (5a-d: EC50 = 0.75–0.81 μM, Ribavirin: EC50 = 3.95 μM for ZIKV and 5a-d: 1.16–2.85 μM, Ribavirin: EC50 = 2.42 μM for CHIKV). The quinolone-N-acylhydrazone hybrids were non-toxic against Vero cells, in which compounds 5c and 5d showed the best selectivities (SI = 1410 and 630 against ZIKV and CHIKV, respectively). Antiviral activity was identified by inhibition of viral RNA production in a dose-dependent manner. In the evaluation of the time of addition of the compounds, we observed that 5b and 5c remain with strong effect even in the addition for 12 h after infection. The above results indicate that quinolone-N-acylhydrazones represent a new and promising class to be further investigated as anti-ZIKV and anti-CHIKV agents.

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.

Conjugate Addition Routes to 2-Alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-Alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates

Under CuBr·SMe2/PPh3 catalysis (5/10 mol-%) RMgCl (R = Me, Et, nPr, CH=CH2, nBu, iBu, nC5H11, cC6H11, Bn, CH2Bn, nC11H23) readily (–78 °C) undergo 1,4-addition to Cbz or Boc protected quinolin-4(1H)-ones to provide 2-alkyl-2,3-dihydroquinolin-4(1H)-ones (14 examples, 54–99 % yield). Asymmetric versions require AlEt3 to Boc-protected ethyl 6-substituted 4(1H)-quinolone-3-carboxylates (6-R group = all halogens, n/i/t-alkyls, CF3) and provide 61–91 % yield, 30–86 % ee; any halogen, Me, or CF3 provide the highest stereoselectivities (76–86 % ee). Additions of AlMe3 or Al(nC8H17)3 provide ≈ 45 and ≈ 75 % ee on addition to the parent (6-R = H). Ligand (S)-(BINOL)P–N(CHPh2)(cC6H11) provides the highest ee values engendering addition to the Si face of the 4(1H)-quinolone-3-carboxylate. Allylation and deprotection of a representative 1,4-addition product example confirm the facial selectivity (X-ray crystallography).