5965-59-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-hydroxyquinoline-2-carboxylate is used as a key intermediate in the synthesis of macro-heterocyclic compounds. These compounds have been identified as potential inhibitors of blood coagulation factor XIa, which plays a crucial role in the coagulation cascade. By inhibiting factor XIa, these macro-heterocyclic compounds can help regulate blood clotting and may be useful in the development of novel therapeutics for conditions related to abnormal blood clotting, such as deep vein thrombosis and stroke.

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

• 67-56-1 methanol 
• 492-27-3 kinurenic acid 
• 4916-29-4 dimethyl 2-(phenyl-amino)-2-butendioate 
• 62-53-3 aniline 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 4916-29-4 dimethyl (Z)-N-(phenyl)aminofumarate 
• 553-90-2 Dimethyl oxalate 
• 551-93-9 2-aminoacetophenone 
• 25007-54-9 Dimethyl 2-oxosuccinate 
• 86119-84-8 phosphoric acid 
• 13593-94-7 kynurenic acid 
• 10567-58-5 dimethyl 2-(phenylamino)maleate 
• 186581-53-3 diazomethane 

Downstream Products

• 102028-50-2 methyl 4-(benzyloxy)quinoline-2-carboxylate 
• 798576-75-7 4-benzyloxyquinoline-2-carboxylic acid [1(S)-(3,4-dibenzyloxy-5-oxo-2,5-dihydrofuran-2(R)-yl)-2-bromoethyl] ester 
• 15733-83-2 4-methoxyquinoline-2-carboxylic acid 
• 139896-91-6 methyl 4-bromoquinoline-2-carboxylate 
• 1354965-44-8 C₁₉H₁₄N₄O₂ 
• 1354965-46-0 C₁₈H₁₂N₄O₂ 
• 13593-94-7 kynurenic acid 
• 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 
• 97909-55-2 methyl-4-aminoquinoline-2-carboxylate 
• 97909-67-6 4-[(E)-4-Chloro-phenoxysulfonylimino]-1,4-dihydro-quinoline-2-carboxylic acid methyl ester 
• 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.

Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism

Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied 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.

COMPOUNDS FOR THE INHIBITION OF CELLULAR PROLIFERATION

Compositions and methods for inhibiting translation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, (4) disorders associated with viral infections, and/or (5) non-proliferative metabolic disorders such as type II diabetes where inhibition of translation initiation is beneficial using the compounds disclosed herein.

Novel tetrahydropyrido[1,2-a]isoindolone derivatives (valmerins): Potent cyclin-dependent kinase/glycogen synthase kinase 3 inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts

The development of CDK and GSK3 inhibitors has been regarded as a potential therapeutic approach, and a substantial number of diverse structures have been reported to inhibit CDKs and GSK-3β in recent years. Only a few molecules have gone through or are currently undergoing clinical trials as CDK and GSK inhibitors. In this paper, we prepared valmerins, a new family containing the tetrahydropyrido[1,2-a]isoindone core. The fused heterocycle was prepared with a straightforward synthesis that was functionalized by a (het)arylurea. Twelve valmerins inhibited the CDK5 and GSK3 with an IC50 100 nM. A semiquantitative kinase scoring was realized, and a cellular screening was done. At the end of our study, we investigated the in vivo potency of one valmerin. Mice exhibited good tolerance to our lead, which proved its efficacy and clearly blocked tumor growth. Valmerins appear also as good candidates for further development as anticancer agents.

Substituent effect of ancillary ligands on the luminescence of bis[4,6-(di-fluorophenyl)-pyridinato-N,C2′]iridium(iii) complexes

Two series of (dfppy)2Ir(LN^O) with different substituents were designed and successfully synthesized and the effect of substitution at the ancillary ligand on the photophysical and electrochemical properties of (dfppy)2Ir

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).