250641-14-6

Usage

Uses

Used in Pharmaceutical Research:
6-Bromoquinoline-2,4-dicarboxylic acid is utilized as a key intermediate in the development of novel anti-cancer or anti-inflammatory agents. Its unique structure and functional groups contribute to its potential as a therapeutic agent, particularly in modulating biological pathways associated with these conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 6-Bromoquinoline-2,4-dicarboxylic acid serves as a building block for the synthesis of various organic compounds. Its versatility in chemical reactions allows for the creation of a wide range of molecules with diverse applications.
Used in Drug Discovery:
6-Bromoquinoline-2,4-dicarboxylic acid is employed as a starting material in drug discovery processes. Its potential biological activity and ability to interact with proteins make it a promising candidate for the development of new pharmaceuticals with targeted effects on specific diseases or conditions.

Upstream product

• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 127-17-3 2-oxo-propionic acid 
• 113-24-6 sodium pyruvate 
• 106-40-1 4-bromo-aniline 
• 38256-25-6 dimethyl (E)-2-oxoglutaconate 
• 13192-04-6 dimethyl 2-ketoglutarate 
• 328-50-7 α-ketoglutaric acid 
• 438590-10-4 2,4-dimethyl 6-bromoquinoline-2,4-dicarboxylate 

Downstream Products

• 927426-19-5 C₂₃H₄BrF₁₀NO₄ 
• 160233-76-1 6-bromoquinoline-4-carboxylic acid 
• 438590-10-4 2,4-dimethyl 6-bromoquinoline-2,4-dicarboxylate 
• 927426-16-2 C₂₇H₇F₁₀NO₄S 

Relevant academic research and scientific papers

Quinoline formamide compound as well as preparation method and application thereof

The invention discloses quinoline formamide compounds as well as a preparation method and application thereof. Specifically, the invention relates to a compound represented by a formula (I) as shown in the specification or a tautomer, a meso-racemate, a r

Inhibitor-conjugated harmonic nanoparticles targeting fibroblast activation protein

The recent progress in the engineering of nanosized inorganic materials presenting tailored physical properties and reactive surface for post-functionalization has opened promising avenues for the use of nanoparticles (NPs) in diagnosis and therapeutic intervention. Surface decoration of metal oxide NPs with ligands modulating circulation time, cellular uptake, affinity and extravasation through active targeting led to efficient cancer specific bioimaging probes. The most relevant cancer biomarkers studied so far include surface and transmembrane cancer cell receptors. More recently, tumor microenvironments and more specifically the fibroblastic element of the tumor stroma have emerged as a valuable target for diagnosis and treatment of several types of cancers. In this study, a low molecular weight ligand targeting fibroblast activation protein α (FAP), which is specifically expressed by activated fibroblasts of the tumor stroma, was synthesized. This ligand demonstrated nanomolar inhibition of FAP with high selectivity with respect to prolyl oligopeptidase (PREP) and dipeptidyl peptidase (DPP) IV, as well as good biocompatibility toward a human lung tissue model. Bismuth ferrite (BFO) harmonic nanoparticles (HNPs) conjugated to this ligand showed target-specific association to FAP as demonstrated by reverse ELISA-type assay using Human Fibroblast Activation Protein alpha/FAP Alexa Fluor 594-conjugated Antibody and multiphoton multispectral microscopy experiments. These functionalized HNPs may provide new nanocarriers to explore the role of FAP in tumorigenesis and to target the fibroblastic component of the tumor microenvironment.

GLUCOSE TRANSPORT INHIBITORS

The present invention relates to quinoline-4-carboxamide derivatives of Formula (I) that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds,

GLUCOSE TRANSPORT INHIBITORS

The present invention relates to chemical compounds that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for

Modulating the interaction between CDK2 and cyclin A with a quinoline-based inhibitor

A new class of quinoline-based kinase inhibitors has been discovered that both disrupt cyclin dependent 2 (CDK2) interaction with its cyclin A subunit and act as ATP competitive inhibitors. The key strategy for discovering this class of protein-protein disrupter compounds was to screen the monomer CDK2 in an affinity-selection/mass spectrometry-based technique and to perform secondary assays that identified compounds that bound only to the inactive CDK2 monomer and not the active CDK2/cyclin A heterodimer. Through a series of chemical modifications the affinity (Kd) of the original hit improved from 1 to 0.005 μM.

Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation

A facile and efficient method for the preparation of 2-non-substituted quinoline-4-carboxylic acids is described via the Pfitzinger reaction of isatins with sodium pyruvate following consequent decarboxylation under microwave irradiation.

Novel high affinity quinoline-based kinase ligands

Quinoline-based inhibitors of cyclin dependent kinase 2, compositions including the inhibitors, and methods of using the inhibitors and inhibitor compositions are described. The inhibitors and compositions including them are useful for treating disease or disease symptoms. The invention also provides for methods of making CDK-2 inhibitor compounds, methods of inhibiting CDK-2, and methods for treating disease or disease symptoms.

Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport

The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl ketoglutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612)1 and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquinolinedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (Ki = 167 μM), 6-PhCH2CH2-QDC (Ki = 143 μM), 6-(4′-phenylstyryl)-QDC (Ki = 64 μM), and 6-biphenyl-4-yl-QDC (Ki=41 μM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.

Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system

Twenty-six quinoline-2,4-dicarboxylic acids (QDC's) were synthesized by a modified Doebner-von Miller pathway and tested as inhibitors against the glutamate vesicular transport (GVT) protein. The QDC's were active as inhibitors with the most potent QDC's found to contain halogens at the 6-/8-position, a hydroxyl at the 8-position, or a tethered aromatic moiety at the 6- or 7-position of the quinoline.