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

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

Downstream Products

• 98948-95-9 6-bromo-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 206257-39-8 6-bromo-4-chloroquinoline-3-carboxylic acid ethyl ester 
• 224175-70-6 ethyl 6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-quinolone-3-carboxylate 
• 1334214-69-5 2-(3-ethoxycarbonyl-1-ethyl-4-oxo-1,4-dihydroquinolin-6-yl)-5,10,15,20-tetraphenylporphyrinatozinc(II) 
• 1462359-46-1 C₁₇H₁₄BrN₃O₄S 
• 1449221-76-4 4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1449221-47-9 N-(4-fluorobenzyl)-4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-48-0 N-(3-fluorobenzyl)-4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-50-4 4-oxo-6-(o-tolyl)-N-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-55-9 4-oxo-6-(o-tolyl)-N-(3-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-53-7 N-(3-bromobenzyl)-4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-59-3 N-(furan-2-ylmethyl)-4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-57-1 4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 
• 1449221-52-6 N-cyclohexyl-4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 

Relevant articles and documents

Sulfonamide-based 4-anilinoquinoline derivatives as novel dual Aurora kinase (AURKA/B) inhibitors: Synthesis, biological evaluation and in silico insights

Aurora kinases (AURKs) were identified as promising druggable targets for targeted cancer therapy. Aiming at the development of novel chemotype of dual AURKA/B inhibitors, herein we report the design and synthesis of three series of 4-anilinoquinoline derivatives bearing a sulfonamide moiety (5a-d, 9a-d and 11a-d). The percent inhibition of AURKA/B was determined for all target quinolines, then compounds showed more than 50percent inhibition on either of the enzymes, were evaluated further for their IC50 on the corresponding enzyme. In particular, compound 9d displayed potent AURKA/B inhibitory activities with IC50 of 0.93 and 0.09 μM, respectively. Also, 9d emerged as the most efficient anti-proliferative analogue in the US-NCI anticancer assay toward the NCI 60 cell lines panel, with broad spectrum activity against different cell lines from diverse cancer subpanels. Docking studies, confirmed that, the sulfonamide SO2 oxygen was involved in a hydrogen bond with Lys162 and Lys122 in AURKA and AURKB, respectively, whereas, the sulfonamide NH could catch hydrogen bond interaction with the surrounding amino acid residues Lys141, Glu260, and Asn261 in AURKA and Lys101, Glu177, and Asp234 in AURKB. Furthermore, N1 nitrogen of the quinoline scaffold formed an essential hydrogen bond with the hinge region key amino acids Ala213 and Ala173 in AURKA and AURKB, respectively.

3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities

Twenty-seven 3-(benzo[d]thiazol-2-yl)-4-aminoquinoline derivatives have been designed and synthesized as topoisomerase I inhibitors. The in vitro anti-proliferation evaluation against four human cancer cell lines (MGC-803, HepG-2, T24, and NCI-H460) and one normal cell line (HL-7702) indicated that most of them exhibited potent cytotoxicity. Among them, 5a was identified as the most promising candidate with a low IC50 value of about 2.20 ± 0.14 and was selected for further exploration. Spectroscopic analyses and agarose-gel electrophoresis assays indicated that 5a could interact with DNA and strongly inhibit topoisomerase I (Topo I). Further screening of the Topo I activity of compounds 5b, 5c, 5e, 5f, 5h, 5i, 5j, 5l, and 5n suggested that some of the compounds might exert quite a different cytotoxicity profile to that of 5a. Molecular modeling studies confirmed that 5a adopts a unique mode to interact with DNA and Topo I. Other molecular mechanistic studies suggested that the treatment of MGC-803 cells with 5a induces S phase arrest, up-regulates the pro-apoptotic protein, down-regulates the anti-apoptotic protein, activates caspase-3, and subsequently induces mitochondrial dysfunction so as to induce cell apoptosis. The in vivo efficiency of 5a was also evaluated on MGC-803 xenograft nude mice and the relative tumor growth inhibition was 42.4percent at 12 mg kg-1 without an obvious loss in the body weight. This journal is

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).