78660-92-1

Usage

Uses

Used in Chemical Synthesis:
2-Biphenyl-4-yl-quinoline-4-carboxylic acid is used as a chemical intermediate for the synthesis of other chemical compounds. Its unique structure, which includes a quinoline ring and a biphenyl moiety, may facilitate the creation of novel molecules with potential applications in various industries.
Used in Pharmaceutical Research:
Although information is limited, 2-Biphenyl-4-yl-quinoline-4-carboxylic acid may be used as a starting material in the development of new pharmaceutical compounds. Its structural features could potentially be exploited to design drugs with specific therapeutic properties, pending further research into its chemical behavior and biological activity.
Used in Material Science:
The potential applications of 2-Biphenyl-4-yl-quinoline-4-carboxylic acid may extend to material science, where its structural components could be utilized in the design of new materials with tailored properties. The carboxylic acid group, in particular, could play a role in the formation of polymers or other composite materials.

InChI:InChI=1/C22H15NO2/c24-22(25)19-14-21(23-20-9-5-4-8-18(19)20)17-12-10-16(11-13-17)15-6-2-1-3-7-15/h1-14H,(H,24,25)

Upstream product

• 312943-44-5 2-(4-iodo-phenyl)-quinoline-4-carboxylic acid 
• 98-80-6 phenylboronic acid 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 91-56-5 indole-2,3-dione 
• 92-91-1 biphenyl-4-acetaldehyde 
• 78660-87-4 3-(2-Biphenyl-4-yl-2-oxo-ethyl)-3-hydroxy-1,3-dihydro-indol-2-one 

Downstream Products

• 1373425-29-6 C₂₉H₂₂N₂O 
• 351327-25-8 2-biphenyl-4-yl-quinoline-4-carboxylic acid hydrazide 
• 627907-12-4 2-biphenyl-4-yl-quinoline-4-carboxylic acid 2-amino-ethyl ester 
• 97257-41-5 methyl 2-([1,1'-biphenyl]-4-yl)quinoline-4-carboxylate 
• 14251-81-1 2-(biphenyl-4-yl)quinoline 
• 97792-53-5 2-biphenyl-4-yl-quinoline-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Design, Synthesis, and Biological Evaluation of 4-Quinoline Carboxylic Acids as Inhibitors of Dihydroorotate Dehydrogenase

We pursued a structure-guided approach toward the development of improved dihydroorotate dehydrogenase (DHODH) inhibitors with the goal of forming new interactions between DHODH and the brequinar class of inhibitors. Two potential residues, T63 and Y356, suitable for novel H-bonding interactions, were identified in the brequinar-binding pocket. Analogues were designed to maintain the essential pharmacophore and form new electrostatic interactions through strategically positioned H-bond accepting groups. This effort led to the discovery of potent quinoline-based analogues 41 (DHODH IC50 = 9.71 ± 1.4 nM) and 43 (DHODH IC50 = 26.2 ± 1.8 nM). A cocrystal structure between 43 and DHODH depicts a novel water mediated H-bond interaction with T63. Additional optimization led to the 1,7-naphthyridine 46 (DHODH IC50 = 28.3 ± 3.3 nM) that forms a novel H-bond with Y356. Importantly, compound 41 possesses significant oral bioavailability (F = 56%) and an elimination t1/2 = 2.78 h (PO dosing). In conclusion, the data supports further preclinical studies of our lead compounds toward selection of a candidate for early-stage clinical development.

Design, synthesis and evaluation of quinoline-based small molecule inhibitor of stat3

As STAT3 has been validated as an anticancer target, its inhibitors have been shown to possess therapeutic promise for the treatment of human cancers. To identify novel and selective STAT3 inhibitors, a virtual screening based on the STAT3 SH2 domain was performed and a small molecule, 2-phenylquinoline-4- carboxylic acid (5a), with an inhibition constant Ki value of 17.53 iM to STAT3 was discovered. On this basis, the derivatives of 5a including esters, amides and dimers were synthesized. The bioactivity and inhibitory selectivity of the derivatives were assayed using human breast cancer cell lines, MDA-MB-468 and MCF-7. Among the derivatives, 5c and 9b showed the most potent inhibitory activity with a good selectivity, and also inhibited STAT3 protein level of MDA-MB-468 cells. The results demonstrated a successful application of virtual screening for lead discovery. Compound 9b might be an effective STAT3 inhibitor lead for the further development of antitumor agents.

Efficient and Recyclable Catalyst of Palladium Nanoparticles Stabilized by Polymer Micelles Soluble in Water for Suzuki-Miyaura Reaction, Ostwald Ripening Process with Palladium Nanoparticles

The Suzuki-Miyaura cross-coupling reaction of ArX (I, Br) with Ar'B(OH)2, catalyzed by Pd-containing water-soluble micelle formed by PS-PEO copolymer and N-cetylpyridinium chloride as a surfactant, was studied in water and methanol. The reaction was performed under mild conditions (temperature up to 50 °C) and the catalyst can be recycled (5 runs) by ultrafiltration without any loss of its catalytic activity. The phenomenon was observed, consisting in growing Pd-nanoparticle size because the small nanoparticles dissolve to form larger nanoparticles in the course of reaction as well as in the presence of the only reagent, ArI. In the latter case, additionally, the formation of very small, not completely dissolved Pd nanoparticles, obviously having a high catalyst activity, is observed. This observation, together with the catalyst activity data might have an implication for a leaching mechanism for the studied catalytic system.

Synthesis of 2-(4-biphenylyl)quinoline-4-carboxylate and carboxamide analogs. New human neurokinin-3 (hNK-3) receptor antagonists

The 2-phenylquinoline-4-carboxamide 1 (Chart 1) has been found to possess moderate affinity for human neurokinin-3 (hNK-3) receptor. In the present work, and in a trial to investigate the effect of the lipophilic moiety at C-2 of the quinoline ring on the