7101-89-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-oxo-1,4-dihydroquinoline-2-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of biologically active compounds. Its presence in the molecular structure can enhance the pharmacological properties of the final drug products, leading to improved therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 4-oxo-1,4-dihydroquinoline-2-carboxylate is utilized as a building block for the preparation of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and weeds, thereby contributing to increased crop yields and protection.
Used in Material Science:
Methyl 4-oxo-1,4-dihydroquinoline-2-carboxylate is employed as a component in the development of functional materials, including organic light-emitting diodes (OLEDs), sensors, and other advanced materials. Its unique structure and properties allow for the creation of materials with specific characteristics, such as improved conductivity, stability, or selectivity.
Used in Drug Development:
Methyl 4-oxo-1,4-dihydroquinoline-2-carboxylate is used as a precursor in the development of new drugs and bioactive molecules. Its pharmacological properties make it a promising candidate for the synthesis of compounds with potential therapeutic applications, including the treatment of various diseases and conditions.

InChI:InChI=1/C11H9NO3/c1-15-11(14)9-6-10(13)7-4-2-3-5-8(7)12-9/h2-6H,1H3,(H,12,13)

Upstream product

• 4916-29-4 dimethyl (Z)-N-(phenyl)aminofumarate 
• 553-90-2 Dimethyl oxalate 
• 551-93-9 2-aminoacetophenone 
• 25007-54-9 Dimethyl 2-oxosuccinate 
• 62-53-3 aniline 
• 86119-84-8 phosphoric acid 
• 4916-29-4 dimethyl 2-(phenyl-amino)-2-butendioate 
• 67-56-1 methanol 
• 13593-94-7 kynurenic acid 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 10567-58-5 dimethyl 2-(phenylamino)maleate 

Downstream Products

• 97909-67-6 4-[(E)-4-Chloro-phenoxysulfonylimino]-1,4-dihydro-quinoline-2-carboxylic acid methyl ester 
• 97909-55-2 methyl-4-aminoquinoline-2-carboxylate 
• 13593-94-7 kynurenic acid 
• 139896-91-6 methyl 4-bromoquinoline-2-carboxylate 
• 1258962-35-4 methyl 1-benzoyl-4-oxo-1,4-dihydro-quinoline-2-carboxylate 
• 1258962-36-5 methyl 1-(4'-methylbenzoyl)-4-oxo-1,4-dihydroquinoline-2-carboxylate 
• 1258962-37-6 methyl 1-(4'-chlorobenzoyl)-4-oxo-1,4-dihydroquinoline-2-carboyxlate 
• 97927-34-9 4-[(E)-Toluene-4-sulfonylimino]-1,4-dihydro-quinoline-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Natural and Unnatural Quinolones Inhibiting the Growth and Motility of Bacteria

Synthesis of a recently discovered S-methylated quinolone natural product (1) was carried out, in addition to the production of a range of 2-substituted 4-quinolone derivatives (2-11). Two approaches were used: (i) the base-catalyzed cyclization of N-(ket

Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes

A unique and efficient method for one-pot synthesis of diverse 4-quinolones from simple and readily available primary anilines and alkynes via Cu(I)-catalyzed direct cyclization has been developed. The (thio)phenols were also found to visible substrates for this reaction. Moreover, an unprecedented synthesis of dihydroepindolidiones has been demonstrated by using secondary anilines as the versatile substrates.

Polyfunctional 4-quinolinones. Synthesis of 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines

We present here two new methods based on rearrangement reactions to obtain novel 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines, an important family of heterocycles with potential applications. Alkyl 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylates were obtained by alkoxide promoted rearrangement of alkyl isatinacetates. A second synthetic route involves the alkoxide promoted reaction of both isatin and N-methylisatin, with alkylating agents having acidic methylenes. This reaction leads to the formation of spiroepoxyoxindoles via Darzens' condensation. When phenacyl bromides are used, the initially obtained benzoyl substituted spiroepoxyoxindoles were smoothly transformed into the corresponding 2-benzoyl-3-hydroxy-4-quinolinones with good to excellent yields.

The synthesis of quinolone natural products from pseudonocardia sp.

The synthesis of four quinolone natural products from the actinomycete Pseudonocardia sp. is reported. The key step involved a sp2-sp3 Suzuki-Miyaura reaction between a common boronic ester lateral chain and various functionalised quinolone cores. The quinolones slowed growth of E. coli and S. aureus by inducing extended lag phases. The total synthesis of four quinolone natural products is reported. The quinolones were synthesised in a highly efficient and direct manner from various readily prepared quinolone cores and a common boronic ester lateral chain. The key step involved a challenging sp2-sp3 Suzuki-Miyaura reaction.

Synthesis and pharmacological evaluation of some 4-Oxo-quinoline-2- carboxylic acid derivatives as anti-inflammatory and analgesic agents

The synthesis and the pharmacological activity of a series of 1-aroyl derivatives of kynurenic acid methyl ester (4-oxo-quinolin-2-carboxy methyl (KYNA) esters), structurally related to NSAID indomethacin are described. The derivatives were screened in vi

Optimized palladium-based approaches to analogues of PK 11195

(Chemical Equation Presented) The peripheral-type benzodiazepine receptor ligands such as PK 11195 and Ro 5-4864 were found more than twenty years ago in the course of research on neurobiology. These ligands were instrumental in pointing out an involvement of the peripheral-type benzodiazepine receptor (PBR) in apoptosis processes. With in mind an improvement of the solubility of PK 11195 in biological media, we report here improved reaction conditions for the palladium-based arylation reaction of alkyl 1-bromoisoquinoline-3-carboxylates and its ethyl 4-bromoquinoline-2-carboxylate isomer. The use of [1,1′-bis(diphenylphosphino) ferrocene] dichloropalladium as a precatalyst enabled a much improved preparation of an array of the 1-arylisoquinoline-3- carboxylates as well as 4-arylquinoline-3-carboxylates. This work should pave the way for the design of chemical probes aiming at the elucidation of the PBR biological role(s).

Kynurenic acid amides as novel NR2B selective NMDA receptor antagonists

A novel series of kynurenic acid amides, ring-enlarged derivatives of indole-2-carboxamides, was prepared and identified as in vivo active NR2B subtype selective NMDA receptor antagonists. The synthesis and SAR studies are discussed.

Kynurenic acid derivatives inhibit the binding of nerve growth factor (NGF) to the low-affinity p75 NGF receptor

The ability of a series of substituted kynurenic acids, thienopyridinonecarboxylic acids, and related compounds to inhibit the binding of nerve growth factor (NGF) to the p75 NGF receptor (NGFR) was evaluated in a radioligand binding assay that utilized a