79607-24-2

Basic information

• Product Name: 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester
• Synonyms: 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester;6-Methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester;Ethyl 6-Methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate;6-methyl-4-carbonylquinoline-3-carboxylic acid ethyl ester
• CAS NO: 79607-24-2
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.25
• Mol File: 79607-24-2.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester(79607-24-2)
• EPA Substance Registry System: 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester(79607-24-2)

Safety Data

• Hazardous Substances Data: 79607-24-2(Hazardous Substances Data)

Usage

General Description

3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester is a chemical compound that is commonly used in the pharmaceutical industry. It is primarily used as an intermediate in the synthesis of various pharmaceuticals, including antimalarial and antitumor drugs. 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester is known for its potent biological activities and is often used in the development of new medicinal products. Its ethyl ester form allows for easy handling and manipulation in laboratory settings, making it a convenient choice for drug synthesis and research purposes. 3-Quinolinecarboxylic acid, 1,4-dihydro-6-methyl-4-oxo-, ethyl ester has the potential to play a significant role in the development of new and effective drug treatments.

Upstream product

• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 106-49-0 p-toluidine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 70145-31-2 ethyl 2-carboethoxy-3-ethoxy-2-propenecarboxylate 

Downstream Products

• 176696-99-4 1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 56824-87-4 ethyl 4-chloro-6-methylquinoline-3-carboxylate 
• 51726-39-7 6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 77779-90-9 8-methyl-2-phenyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774585-93-2 2-(4-methoxyphenyl)-8-methyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774585-95-4 2-(4-bromo-phenyl)-8-methyl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one 
• 77779-92-1 2-(4-chloro-phenyl)-8-methyl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one 
• 774585-94-3 2-(4-fluorophenyl)-8-methyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774585-85-2 8-methyl-2-phenyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774585-99-8 8-methyl-2-(4-chlorophenyl)-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774585-98-7 8-methyl-2-(4-fluorophenyl)-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774585-97-6 8-methyl-2-(4-methoxyphenyl)-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 774586-00-4 8-methyl-2-(4-bromophenyl)-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 

Relevant articles and documents

Conventional and microwave prompted synthesis, antioxidant, anticholinesterase activity screening and molecular docking studies of new quinolone-triazole hybrids

The synthesis of ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylates (4, 5) was performed via the reaction of corresponding anilines with diethyl ethoxymethylenemalonate under conventional and also microwave promoted conditions. The treatment of 4 and 5 affor

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.

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).