30160-03-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl -2-Methylquinoline-3-carboxylate is used as a key intermediate in the synthesis of quinoline-based p300 histone acetyltransferase inhibitors. These inhibitors play a crucial role in promoting apoptosis, or programmed cell death, in human leukemia U937 cells. By targeting and inhibiting specific enzymes, Methyl -2-Methylquinoline-3-carboxylate contributes to the development of novel therapeutic strategies for the treatment of leukemia and potentially other cancer types.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 529-23-7 o-aminobenzaldehyde 
• 79237-43-7 1,1-Diethoxy-1,2-dihydro-cyclobuta[b]quinoline 
• 80742-11-6 6-Methyl-2,4-bis-(2-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-5-carbonsaeuremethylester 
• 67-56-1 methanol 
• 635-79-0 2-methylquinoline-3-carboxylic acid 
• 21731-17-9 methyl 3-aminocrotonate 
• 957374-57-1 (+/-)-methyl 2-(2-nitrobenzyl)-3-oxobutanoate 
• 552-89-6 2-nitro-benzaldehyde 
• 271-58-9 anthranil 
• 26260-02-6 2-iodobenzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 79237-40-4 3-bromo-2,2-dichloro-1'-formyl-1',2',3',4'-tetrahydrospiro 

Downstream Products

• 53936-95-1 3-(hydroxymethyl)-2-methylquinoline 
• 134340-92-4 2-methylquinoline-3-carbohydrazide 
• 264189-55-1 3-ethoxy-1,3-dihydrofuro[4,3-b]quinoline 
• 57032-14-1 2-hydroxymethyl-quinolin-3-yl-methanol 
• 883557-34-4 {5-[2-((E)-2-Pyridin-4-yl-vinyl)-quinolin-3-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine 
• 883557-57-1 (4-tert-butyl-phenyl)-{5-[2-(2-pyridin-4-yl-vinyl)-quinolin-3-yl]-[1,3,4]oxadiazol-2-yl}-amine 
• 883556-84-1 [5-(2-methyl-quinolin-3-yl)-[1,3,4]oxadiazol-2-yl]-(3-trifluoromethyl-phenyl)-amine 
• 883556-94-3 (4-tert-butyl-phenyl)-[5-(2-methyl-quinolin-3-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 950919-15-0 C₂₇H₂₇NO₂Si 
• 950919-16-1 C₃₉H₃₅N₃O₃Si 

Relevant academic research and scientific papers

Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.

Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14–23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.

Synthesis of quinolines: Via copper-catalyzed domino reactions of enaminones

Quinoline derivatives were obtained from enaminones and 2-bromo- or 2-iodobenzaldehydes via copper-catalyzed domino reactions consisting of the aldol reaction, C(aryl)-N bond formation and elimination. The electronic effect of aldehydes played a major role in the reaction outcome. Two simple protocols are disclosed to achieve various quinolines from both cyclic and acyclic enaminones in good yields. With the less-reactive acyclic enaminones, diethyl-2-(2-bromobenzylidene)malonate was shown to be more compatible than the benzaldehydes.

Quinoline- and 1,8-naphthyridine-3-carboxylic acids using a self-catalyzed Friedl?nder approach

One-step syntheses of 2-alkyl- and 2,4-dialkyl-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids are reported using a catalyst-free Friedl?nder reaction. The reaction is carried out in one step by simple heating of 2-aminobenzaldehyde, 2-amino-5-chlorobenzaldehyde, 2-aminonicotinaldehyde, or 2-aminoacetophenone with a β-ketoester in toluene or xylene for 24 h. Under these conditions, the carboxylic acid product is isolated directly from the reaction mixture without need for further purification. The observation that the reaction starts slowly and accelerates as it proceeds suggests that the transformation is self-catalyzed. This hypothesis is also supported by the finding that attempts to extend the current reaction to diketones, which cannot hydrolyze to an acid, were generally unsuccessful.

Quinoline-based p300 histone acetyltransferase inhibitors with Pro-apoptotic activity in human leukemia U937 cells

Chemical manipulations performed on 2-methyl-3-carbethoxyquinoline (1), a histone acetyltransferase inhibitor previously identified by our research group and active at the sub-millimolar/millimolar level, led to compounds bearing higher alkyl groups at th

Iron/acetic acid mediated intermolecular tandem C-C and C-N bond formation: An easy access to acridinone and quinoline derivatives

An efficient iron/acetic acid mediated one pot reductive cyclization protocol was successfully developed for the synthesis of acridinone and quinoline derivatives. This highly efficient process proceeds under mild conditions, tolerates different functiona

Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents

The current study reports design and diversity oriented synthesis of novel bis heterocycles with a common 2-methyl, C-4 unsubstituted quinoline moiety as the central key heterocycle. Employing reagent based skeletal diversity approach; a facile synthesis

Synthesis of quinolines via friedlaender reaction in water and under catalyst-free conditions

A straightforward and efficient method for the synthesis of quinolines via Friedlaender reaction of 2-aminobenzaldehyde with various ketones or malononitrile in water without using any catalyst at 70 °C is reported. Georg Thieme Verlag Stuttgart New York.

(±)-2-Alkyl-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a catalyst and pressure dependent tandem reduction-reductive amination reaction

(Chemical Equation Presented) A series of 2-(2-nitrobenzyl)-substituted β-keto ester derivatives has been subjected to reductive cyclization under catalytic hydrogenation conditions. The reactions were found to be highly dependent on the catalyst and hydr

Synthesis of an analogue of lavendamycin and of conformationally restricted derivatives by cyclization via a hemiaminal intermediate

Quinoline 12 was obtained by a Friedl?nder reaction from 2-aminobenzaldehyde and methyl acetoacetate. Reduction, silylation then oxidation provided compound 8a. A Pictet-Spengler reaction between the latter and tryptophan methyl ester yielded compound 14,