4546-48-9

Usage

Uses

Used in Pharmaceutical and Fine Chemical Synthesis:
2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID METHYL ESTER is used as a building block for the synthesis of various pharmaceuticals and fine chemicals, leveraging its structural versatility to create compounds with potential therapeutic applications.
Used in Drug Discovery and Medicinal Chemistry:
In the field of drug discovery and medicinal chemistry, 2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID METHYL ESTER is utilized as a key component in the development of new drugs, due to its ability to interact with biological targets and contribute to the creation of effective medicinal agents.
Used as a Fluorescent Probe:
2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID METHYL ESTER is also used as a fluorescent probe in research settings, where its optical properties can be harnessed for the detection and analysis of biological processes or molecular interactions.
Used as an Intermediate in Quinoline Derivative Production:
Furthermore, 2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID METHYL ESTER serves as an intermediate in the production of other functionalized quinoline derivatives, which can be applied in various chemical and pharmaceutical processes to yield specialized compounds with unique properties.

InChI:InChI=1/C17H13NO2/c1-20-17(19)14-11-16(12-7-3-2-4-8-12)18-15-10-6-5-9-13(14)15/h2-11H,1H3

Upstream product

• 132-60-5 cinchophen 
• 67-56-1 methanol 
• 59661-86-8 2-phenylquinoline-4-carbonyl chloride 
• 292638-85-8 acrylic acid methyl ester 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 600-22-6 pyruvic acid methyl ester 
• 4519-46-4 methyl 2-bromoacrylate 
• 36997-05-4 2-methoxyacrylic acid ethyl ester 
• 62-53-3 aniline 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 922-67-8 propynoic acid methyl ester 
• 4098-17-3 1-(1-azido-2-iodoethyl)benzene 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 

Downstream Products

• 855167-11-2 2-phenyl-quinoline-4-carboxylic acid-(2-benzo[1,3]dioxol-5-yl-ethylamide) 
• 29268-33-5 4-hydroxymethyl-2-phenylquinoline 
• 5855-52-7 2-phenylquinolin-4-amine 
• 838828-67-4 2-(2-phenyl-[4]quinolyl)-propan-2-ol 
• 838828-68-5 2-isopropenyl-2-phenylquinoline 
• 854386-52-0 5-(2-phenyl-[4]quinolyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 80221-48-3 2-[3(R)-ethenyl-4(S)-piperidyl]-1-(2-phenyl-4-quinolyl) ethanone 
• 1415314-26-9 1,1,1,3,3,3-hexafluoro-2(2-phenylquinolin-4-yl)propan-2-ol 

Relevant academic research and scientific papers

Synthesis of substituted quinolines via B(C6F5)3-catalyzed aniline-aldehyde-pyruvate oxidative annulation

A metal-free method to construct quinoline derivatives via B(C6F5)3-catalyzed cyclization of anilines with aldehyde derivatives and pyruvates is described. This three-component cascade reaction provides an efficient approa

Palladium-Catalyzed Three-Component Cascade Reaction of Nitriles: Synthesis of 2-Arylquinoline-4-carboxylates

A new method for converting easy availability starting materials 2-(2-oxoindolin-3-yl)acetonitrile, arylboronic acids, and alcohols into 2-arylquinoline-4-carboxylates is reported. The procedure involves a three-component addition/ring expansion/esterification reaction in the presence of Pd(II) catalyst with high functional group tolerance under mild conditions. In addition, the photophysical properties of the resulting product were investigated and exhibited excellent polarity-sensitive fluorescence properties and AIE property.

The remarkable selectivity of the 2-arylquinoline-based acyl hydrazones toward copper salts: Exploration of their catalytic applications in the copper catalysed: N -arylation of indole derivatives and C1-alkynylation of tetrahydroisoquinolines via the A

Ligands promoting copper-catalysed coupling reactions have received increasing attention because of their ability to enhance the catalytic activity of copper, making these reactions applicable in different fields such as drugs, pharmaceutically interestin

Ethyl lactate-involved three-component dehydrogenative reactions: Biomass feedstock in diversity-oriented quinoline synthesis

Three-component reactions of ethyl/methyl lactate, anilines and aldehydes providing quinolines have been developed via simple iron(iii) chloride catalysis without using an additional organic medium or external oxidant. This three-component protocol shows

Selective Methylation of Arenes: A Radical C?H Functionalization/Cross-Coupling Sequence

A selective, nonchelation-assisted methylation of arenes has been developed. The overall transformation, which combines a C?H functionalization reaction with a nickel-catalyzed cross-coupling, offers rapid access to methylated arenes with high para selectivity. The reaction is amenable to late-stage methylation of small-molecule pharmaceuticals.

Triple zirconocene/br?nsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C-C formative cyclization/oxidation

A new triple cooperative and relay catalysis system featuring the Mannich addition followed by C-C construction and oxydehydrogenation is described. The zirconocene dichloride and trimellitic acid synergic catalysis triggered the Mannich addition and C-C bond construction reactions, while CuO allowed relay catalysis for oxydehydrogenation. This novel strategy demonstrated superior activity for the synthesis of substituted quinolines from commercially available anilines, aldehydes and ketones. The corresponding substituted quinolines were synthesized with 32 examples in 90-96% yields under mild reaction conditions. A novel zirconocene-Br?nsted acid complex, generated in situ and acting as an active catalyst, was validated from the mechanistic studies.

Convergent synthesis and cytotoxicity of novel trifluoromethyl-substituted (1H-pyrazol-1-yl)(quinolin-4-yl) methanones

A convergent synthesis of a series of 16 new polysubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)(quinolin-4-yl)methanones, starting from isatin and alky(aryl/heteroaryl) ketones, is described. The diheteroaryl methanones were achieved at yields of up to 95% by a [3?+?2] cyclocondensation reaction involving 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluorobut-3-en-2-ones (by two-step reaction) and 2-alkyl(aryl/heteroaryl)-4-carbohydrazides (by three-step reaction). Subsequently, representative dehydrated heterocyclic derivatives were obtained from the respective 5-hydroxy-2-pyrazoline moieties by classical dehydration reactions, which resulted in the corresponding (5-(trifluoromethyl)-1H-pyrazol-1-yl)(quinolin-4-yl)methanones (three examples) at yields of 69–82%. The subsequent cytotoxicity evaluation showed that compounds with aromatic groups at the 2-position of the quinoline and a methyl moiety at the 3-position of the pyrazole have significant cytotoxicity in human leukocytes at high concentrations (200?μM).

Method for efficiently preparing polysubstituted quinoline by synergy of copper oxide and zirconocene double-acid system

The invention discloses a method for efficiently preparing polysubstituted quinoline by synergy of copper oxide and a zirconocene double-acid system. According to the method, a mixed solution of water and isopropyl alcohol is taken as a solvent, a compound formed by biszirconium dichloride and a benzoic acid ligand is taken as a double-acid catalyst, and aromatic amine, aldehyde and ketone are efficiently catalyzed by the double-acid catalyst to be reacted to prepare the polysubstituted quinoline under the synergistic effect of copper oxide. The method is wide in substrate application range, mild in reaction condition, short in time and high in atom economy, the raw materials are low in cost and readily available, the catalyst is stable, low in cost and nontoxic for water and the air, a novel low-cost, green and efficient means is provided for preparation of the polysubstituted quinoline, and the prepared polysubstituted quinoline has a great application potential to preparation of a medicament, a natural product, a luminous material and an organic synthetic intermediate.

Phosphorescent biscyclometallated iridium(iii) ethylenediamine complexes functionalised with polar ester or carboxylate groups as bioimaging and visualisation reagents

We report the synthesis, characterisation and photophysical properties of new phosphorescent biscyclometallated iridium(iii) ethylenediamine (en) complexes functionalised with polar ester or carboxylate groups [Ir(N^C)2(en)]n(X) (n = +1, X = Cl-, HN^C = methyl 4-(2-pyridyl)benzoate Hppy-COOMe (1a), methyl 2-phenyl-4-quinolinecarboxylate Hpq-COOMe (2a); n = -1, X = Li+, HN^C = 4-(2-pyridyl)benzoate Hppy-COO- (1b), 2-phenyl-4-quinolinecarboxylate Hpq-COO- (2b)). In aqueous solutions, the carboxylate complexes 1b and 2b displayed emission quenching (ca. 7 and 74 fold, respectively) and lifetime shortening upon protonation, and their pKa values were determined to be 5.13 and 3.46, respectively. The pq complexes 2a and 2b exhibited hypsochromic shifts in their emission maxima and a significant increase in emission intensity (ca. 84 and 15 fold, respectively) upon nonspecific binding to the protein bovine serum albumin (BSA). Inductively coupled plasma-mass spectroscopy (ICP-MS) and laser-scanning confocal microscopy (LSCM) results revealed that the ester complexes 1a and 2a were efficiently internalised by the human cervix epithelioid carcinoma (HeLa) cells through energy-requiring pathways and subsequently localised in endosomes and mitochondria, respectively. They showed good biocompatibility in the dark, but became significantly cytotoxic upon photoirradiation due to the generation of singlet oxygen. In contrast, in aqueous solutions of physiological pH, the carboxylate complexes 1b and 2b existed as the anionic form and hardly entered cells due to limited membrane permeability, as evidenced by the intense emission surrounding the plasma membrane of the cells. They showed negligible cytotoxicity and the cell viability remained over 95% for an incubation period of 24 hours. In view of the low cytotoxicity and strongly emissive nature of the hydrophilic ppy-COO- complex 1b in an aqueous medium, the potential application of the complex as a visualisation reagent has been demonstrated using zebrafish (Danio rerio) as an animal model. This journal is

Synthesis of Quinolines by Visible-Light Induced Radical Reaction of Vinyl Azides and α-Carbonyl Benzyl Bromides

A visible-light induced radical reaction of vinyl azides and α-carbonyl benzyl bromides was developed, which provides an efficient route to polysubstituted quinolines via a C-C and C-N bond formation sequence.