4364-02-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID is used as a potential pharmaceutical compound for its possible bioactivity. The presence of quinoline and carboxylic acid groups in its structure suggests that it may have therapeutic applications, although further research is needed to determine its specific uses and effectiveness.
Used in Chemical Industry:
2-(4-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID is used as a chemical intermediate or building block in the synthesis of more complex molecules. Its unique structure, which includes both quinoline and carboxylic acid groups, may be utilized in the development of new chemical products or materials.

InChI:InChI=1/C17H13NO3/c1-21-12-8-6-11(7-9-12)16-10-14(17(19)20)13-4-2-3-5-15(13)18-16/h2-10H,1H3,(H,19,20)

Upstream product

• 91-56-5 indole-2,3-dione 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 62-53-3 aniline 
• 98-86-2 acetophenone 
• 42366-35-8 hydroxyimino-N-phenylacetamide 

Downstream Products

• 838-34-6 2-(p-methoxyphenyl)benzoxazole 
• 6952-34-7 2-(4-hydroxyphenyl)-quinoline-4-carboxylic acid 
• 51842-82-1 2-(4-methoxyphenyl)quinoline-4-carboxamide 
• 95201-25-5 ethyl 2-(4-methoxyphenyl)quinoline-4-carboxylate 
• 148887-64-3 {[2-(4-Methoxy-phenyl)-quinoline-4-carbonyl]-methyl-amino}-acetic acid ethyl ester 
• 30696-03-8 2-(4-hydroxyphenyl)quinoline 
• 858474-14-3 (1R,2R)-(2-(4-methoxyphenyl)quinolin-4-yl)(piperidin-2-yl)methanol hydrochloride 
• 1384275-34-6 threo-tert-butyl 2-(hydroxy(2-(4-methoxyphenyl)quinolin-4-yl)methyl)piperidine-1-carboxylate 
• 1384275-32-4 C₂₇H₃₂N₂O₄ 
• 1609280-29-6 C₇₂H₆₄Cd₂N₄O₁₆ 
• 803640-64-4 2-(4-Methoxy-phenyl)-quinoline-4-carbonyl chloride 

Relevant academic research and scientific papers

Quinoline-4-carboxamide skeleton derivative and application thereof

The invention discloses a quinoline-4-formamide skeleton derivative and application thereof, belonging to the field of chemical medicines. The invention provides a compound as shown in a formula I or pharmaceutically acceptable salt thereof. The invention

Design and synthesis of novel quinoline/chalcone/1,2,4-triazole hybrids as potent antiproliferative agent targeting EGFR and BRAFV600E kinases

New quinoline / chalcone hybrids containing 1,2,4-triazole moiety have been designed, synthesized and their structures elucidated and confirmed by various spectroscopic techniques. The designed compounds showed moderate to good activity on different NCI 60 cell lines in a single-dose assay with a growth inhibition rate ranging from 50% to 94%. Compounds 7b, 7d, 9b, and 9d were the most active compounds in most cancer cell lines with a growth inhibition percent between 77% and 94%. Newly synthesized hybrids were evaluated for their anti-proliferative activity against a panel of four human cancer cell lines. Compounds 7a, 7b, 9a, 9b, and 9d showed promising antiproliferative activities. These compounds were further tested for their inhibitory potency against EGFR and BRAFV600E kinases with erlotinib as a reference drug. The molecular docking study of compounds 7a, 7b, 9a, 9b, and 9d revealed nice fitting into the active site of EGFR and BRAFV600E kinases. Compounds 7b, 9b, and 9d displayed the highest binding affinities and similar binding pattern to those of erlotinib.

Synthesis of Novel Quinoline–Benzoxazolinone Ester Hybrids: In Vitro Anti-Inflammatory Activity and Antibacterial Activity

Abstract: A series of novel quinoline-benzoxazolinone ester hybrids were synthesized characterized and assessed for their in vitro anti-inflammatory and antibacterial activity. The in vitro anti-inflammatory activity was executed using protein denaturation assay, proteinase inhibitory assay and human red blood cell membrane stabilization assay. Most of the compounds exhibited potential anti-inflammatory activity. Compound (2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(thiophen-2-yl)quinoline-4-carboxylate showed a better anti-inflammatory activity than the standard drugs diclofenac sodium and indomethacin. Furthermore, antibacterial activities of the synthesized compounds were evaluated using resazurin microtiter assay (REMA) and were compared with a positive drug standard chloramphenicol. The compounds demonstrated moderate to potent antibacterial activity. (2-Oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(3,4-dimethoxyphenyl)quinoline-4-carboxylate and (2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(2-chlorophenyl)quinoline-4-carboxylate displayed excellent activity against all bacterial strains in comparison to standard chloramphenicol. Moreover, cytotoxicity was performed on MDCK cells using MTT assay and it was found that none of the synthesized derivatives possessed any cytotoxicity.

New quinoline/1,2,4-triazole hybrids as dual inhibitors of COX-2/5-LOX and inflammatory cytokines: Design, synthesis, and docking study

A novel series of 19 quinoline/1,2,4-triazole hybrid 6a-i and 7a-j was synthesized and evaluated in vitro as dual COX-2/5-LOX inhibitors. Compounds 6e, 6i, and 7e displayed the highest potency and selectivity for inhibiting COX-2 activity (IC50 = 7.25, 8.13, and 8.48 nM, respectively; selectivity index (COX-1/COX-2) = 44.89, 30.30, and 33.47, respectively) in comparison to celecoxib (COX-2 IC50 = 42.60 nM; selectivity index (SI) = 8.05). The anti-inflammatory activity of the newly synthesized compounds was further examined in vivo using a carrageenan induced paw edema assay. Interestingly, the in vitro findings of the COX inhibitory assay were consistent with the in vivo assay. Moreover, 6e, 6i, and 7e showed a substantial reduction in serum concentrations of PGE2, TNF-α, IL-6. Molecular docking analysis of compounds 6e, 6f, 6i, 7e, and 7f revealed high binding affinities toward COX-2 compared to COX-1, which was matched with the experimental results. In addition, these compounds exhibited different binding orientations into the active site of COX-2, which were dependent on the type of substitutions on N4 of the triazole ring. Among the tested derivatives, compounds 6e, 6i and 7e which showed high selectivity to COX-2, exhibited hydrogen bonding interactions with key amino acids in COX-2 such as Arg120, Arg513, and/or Glu524. In addition, the tested compounds also showed multiple hydrogen bonds with the Arg101, Val110, Arg138 or His130 in 5-LOX. These findings show, taken together, that those derivatives are good leads to potential anti-inflammatory agents with lowest gastric damage.

NO-releasing STAT3 inhibitors suppress BRAF-mutant melanoma growth

Constitutive activation of STAT3 can play a vital role in the development of melanoma. STAT3-targeted therapeutics are reported to show efficacy in melanomas harboring the BRAFV600E mutant and also in vemurafenib-resistant melanomas. We designed and synthesized a series of substituted nitric oxide (NO)-releasing quinolone-1,2,4-triazole/oxime hybrids, hypothesizing that the introduction of a STAT3 binding scaffold would augment their cytotoxicity. All the hybrids tested showed a comparable level of in vitro NO production. 7b and 7c exhibited direct binding to the STAT3-SH domain with IC50 of ～ 0.5 μM. Also, they abrogated STAT3 tyrosine phosphorylation in several cancer cell lines, including the A375 melanoma cell line that carries the BRAFV600E mutation. At the same time, they did not affect the phosphorylation of upstream kinases or other STAT isoforms. 7c inhibited STAT3 nuclear translocation in mouse embryonic fibroblast while 7b and 7c inhibited STAT3 DNA-binding activity in the A375 cell line. Their anti-proliferating activity is attributed to their ability to trigger the production of reactive oxygen species and induce G1 cell cycle arrest in the A375 cell line. Interestingly, 7b and 7c showed robust cell growth suppression and apoptosis induction in two pairs of BRAF inhibitor-na?ve (-S) and resistant (-R) melanoma cell lines containing a BRAF V600E mutation. Surprisingly, MEL1617-R cells that are known to be more resistance to MEK inhibition by GSK1120212 than MEL1617-S cells exhibit a similar response to 7b and 7c.

Discovery of Potent Small-Molecule SIRT6 Activators: Structure-Activity Relationship and Anti-Pancreatic Ductal Adenocarcinoma Activity

SIRT6 activation is thought to be a promising target for the treatment of many diseases, particularly cancer. Herein, we report the discovery of a series of new small-molecule SIRT6 activators. Structure-activity relationship analyses led to the identific

New quinoline/chalcone hybrids as anti-cancer agents: Design, synthesis, and evaluations of cytotoxicity and PI3K inhibitory activity

A series of quinoline-chalcone hybrids was designed as potential anti-cancer agents, synthesized and evaluated. Different cytotoxic assays revealed that compounds experienced promising activity. Compounds 9i and 9j were the most potent against all the cell lines tested with IC50 = 1.91–5.29 μM against A549 and K-562 cells. Mechanistically, 9i and 9j induced G2/M cell cycle arrest and apoptosis in both A549 and K562 cells. Moreover, all PI3K isoforms were inhibited non selectively with IC50s of 52–473 nM when tested against the two mentioned compounds with 9i being most potent against PI3K-γ (IC50 = 52 nM). Docking of 9i and 9j showed a possible formation of H-bonding with essential valine residues in the active site of PI3K-γ isoform. Meanwhile, Western blotting analysis revealed that 9i and 9j inhibited the phosphorylation of PI3K, Akt, mTOR, as well as GSK-3β in both A549 and K562 cells, suggesting the correlation of blocking PI3K/Akt/mTOR pathway with the above antitumor activities. Together, our findings support the antitumor potential of quinoline-chalcone derivatives for NSCLC and CML by inhibiting the PI3K/Akt/mTOR pathway.

Synthesis and Luminescent Properties of Eu3+, Gd3+, and Tb3+ Complexes with Quinoline-4-carboxylic Acids

New complex compounds LnL3·nH2O (n = 5–10) have been synthesized on the basis of Eu3+, Gd3+, and Tb3+ salts and quinoline-4-carboxylic acid derivatives obtained via the Pfitzinger reaction. Compositio

Synthesis, characterization, and antileishmanial activity of certain quinoline-4-carboxylic acids

Leishmaniasis is a fatal neglected parasitic disease caused by protozoa of the genus Leishmania and transmitted to humans by different species of phlebotomine sandflies. The disease incidence continues to increase due to lack of vaccines and prophylactic drugs. Drugs commonly used for the treatment are frequently toxic and highly expensive. The problem of these drugs is further complicated by the development of resistance. Thus, there is an urgent need to develop new antileishmanial drug candidates. The aim of this study was to synthesize certain quinoline-4-carboxylic acids, confirm their chemical structures, and evaluate their antileishmanial activity. Pfitzinger reaction was employed to synthesize fifteen quinoline-4-carboxylic acids (Q1-Q15) by reacting equimolar mixtures of isatin derivatives and appropriate α-methyl ketone. The products were purified, and their respective chemical structures were deduced using various spectral tools (IR, MS, 1H NMR, and 13C NMR). Then, they were investigated against L. donovani promastigote (clinical isolate) in different concentration levels (200 μg/mL to 1.56 μg/mL) against sodium stibogluconate and amphotericin B as positive controls. The IC50 for each compound was determined and manipulated statistically. Among these compounds, Q1 (2-methylquinoline-4-carboxylic acid) was found to be the most active in terms of IC50.

COMPOUNDS FOR TREATMENT OF GLIOBLASTOMA

The present invention relates to compounds and methods for the treatment of glioblastoma, as well as to a pharmaceutical composition comprising said compounds. More specifically the invention relates to substituted quinoline derivatives having the formula (I), (II) or (III), and a pharmaceutical composition comprising said compounds for the treatment of cancer. (Formulae (I), (II), (III))