5466-31-9

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-CHLORO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID is used as a potential drug candidate for its pharmacological and therapeutic properties. Its quinoline structure and functional groups contribute to its potential as a lead compound in the development of new medications.
Used in Antiviral Applications:
In the field of antiviral research, 2-(4-CHLORO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID is used as a potential antiviral agent due to the biological activities exhibited by quinoline derivatives, which include antiviral properties.
Used in Anticancer Applications:
2-(4-CHLORO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID is used as a potential anticancer agent, leveraging the anticancer properties often found in quinoline derivatives. Its structure may allow for the targeting of specific cancer cells or pathways, offering a new avenue for cancer treatment.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, 2-(4-CHLORO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID serves as a subject for further research and development. Its unique structure and functional groups make it a valuable compound for exploring new drug mechanisms and therapeutic approaches.

InChI:InChI=1/C16H10ClNO2/c17-11-7-5-10(6-8-11)15-9-13(16(19)20)12-3-1-2-4-14(12)18-15/h1-9H,(H,19,20)/p-1

Upstream product

• 91-56-5 indole-2,3-dione 
• 99-91-2 para-chloroacetophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 62-53-3 aniline 

Downstream Products

• 24698-70-2 2-(4-chlorophenyl)quinoline 
• 854864-03-2 2-(4-chloro-phenyl)-quinoline-4-carbonyl chloride 
• 148887-65-4 {[2-(4-Chloro-phenyl)-quinoline-4-carbonyl]-methyl-amino}-acetic acid ethyl ester 
• 1415834-93-3 4-carboxy-2-(4-chlorophenyl)-1-(2-oxo-2-phenylethyl)quinolinium iodide 
• 1415834-96-6 1-(2-(carbamothioylhydrazono)-2-phenylethyl)-4-carboxy-2-(4-chlorophenyl)quinolinium iodide 
• 1415834-99-9 1-((2-(4-(4-aminophenyl)thiazol-2(5H)-ylidene)hydrazono)-2-phenylethyl)-4-carboxy-2-(4-chlorophenyl)quinolinium iodide 
• 1415835-09-4 7-(4-chlorophenyl)-5,6-diphenylbenzo[h][1, 2, 4]triazolo[3,4-a][2, 6]napthyridin-3(2H)-one 
• 1415835-12-9 7-(4-chlorophenyl)-5,6-diphenylbenzo[h][1, 2, 4]triazolo[3,4-a][2, 6]naphthyridin-3(2H)-thione 
• 1415835-02-7 4-carboxy-2-(4-chlorophenyl)-1-(2-phenyl-2-(4-phenylthiazol-2(5H)-ylidene)hydrazono)ethylquinolinium iodide 
• 1415835-05-0 5-(4-chlorophenyl)-3,4-diphenyl-1H-Pyrana[4,3-c] quinolin-1-one 
• 80221-37-0 methyl‐2‐(4‐chlorophenyl)quinoline‐4‐carboxylate 
• 5428-80-8 [2-(4-chlorophenyl)quinolin-4-yl]-piperidin-2-yl-methanol 

Relevant academic research and scientific papers

Discovery of novel tubulin inhibitors targeting the colchicine binding site via virtual screening, structural optimization and antitumor evaluation

The colchicine binding site of tubulin is a promising target for discovering novel antitumor agents which exert the antiangiogenic effect and are not susceptible to multidrug resistance. For identifying novel tubulin inhibitors, structure-based virtual screening was applied to identify hit 9 which displayed moderate tubulin polymerization inhibition and broad-spectrum in vitro antitumor activity. Structural optimization was performed, and biological assay revealed analog E27 displayed the best antitumor activity with IC50 values ranging from 7.81 μM to 10.36 μM, and improved tubulin polymerization inhibitory activity (IC50 = 16.1 μM). It significantly inhibited cancer cell migration and invasion, induced cell apoptosis and arrested the cell cycle at G2/M phase. Moreover, the apoptotic effect of E27 is related to the increased ROS level, the decrease of MMP, and the abnormal expression of apoptosis-related proteins. Taken together, these results suggested E27 was a promising lead compound for discovering novel tubulin-targeted antitumor agents.

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.

A green synthesis of quinoline-4-carboxylic derivatives using p-toluenesulfonic acid as an efficient organocatalyst under microwave irradiation and their docking, molecular dynamics, ADME-Tox and biological evaluation

P-Toluenesulfonic acid, being an efficient, nonhazardous, and fast accessible organocatalyst, was used for the preparation of quinoline-4-carboxylic acid derivatives via a one-pot three-component reaction of aromatic benzaldehyde, substituted aniline, and pyruvic acid under microwave irradiation. After completion of the reaction, the pure products were isolated by column chromatography. Here, to achieve the desired synthesis, various catalytic and solvent conditions were applied to perform a comparison study. We are using higher yield, simple work-up process, avoiding the use of hazardous organic solvents, short reaction time and higher advantages of the present protocol in the study. Biological activities of synthesized compounds were tested against various antibacterial, antifungal, antimalarial, and antituberculosis strains. Compounds 4a and 4c (MIC 50 μg/mL) and compounds 4d and 4n (MIC 62.5 μg/mL) were found active against the Escherichia coli strain, compounds 4c and 4p (MIC 25 μg/mL) were found active against the Staphylococcus aureus strain, and compounds 4c and 4d were found active against the Plasmodium falciparum strain. Molecular docking revealed that ligands and proteins fitted exactly in the binding pocket and had significant correlation with the biological activity. We have also tested molecular dynamics and ADME-Tox parameters for the synthesized compounds.

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.

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))

Energy efficient Pfitzinger reaction: A novel strategy using a surfactant catalyst

A novel energy efficient method for the Pfitzinger reaction is demonstrated, which is catalysed using a surfactant, cetyltrimethylammonium hydroxide. The surfactant nature of the catalyst caused the substrate to be soluble in aqueous media, which enhanced the interaction of the catalyst with the substrate. An increase in the rate of reaction and more than 78% of energy saving were observed under ultrasonic irradiation.

COMPOUNDS AND USE FOR TREATING CANCER

The present invention relates to certain 2,4-disubstituted quinoline derivatives, to their therapy, as well as to pharmaceutical compositions comprising said compounds. More specifically the invention relates to certain 2,4-disubstituted quinoline derivatives or pharmaceutical compositions comprising said compounds for the treatment of cancers characterized by overactive Ras and/or Rac or signalling pathway.