1647-88-7

Upstream product

• 443-69-6 5-fluoro-1H-indole-2,3-dione 
• 98-86-2 acetophenone 
• 371-40-4 4-fluoroaniline 
• 2146-07-8 p-fluoroaniline hydrochloride 
• 351-09-7 N-(4-fluorophenyl)-2-(hydroxyimino) acetamide 
• 100-52-7 benzaldehyde 
• 127-17-3 2-oxo-propionic acid 

Downstream Products

• 2558-26-1 6-fluoro-2-phenylquinoline 
• 1453173-04-0 C₁₆H₉ClFNO 

Relevant academic research and scientific papers

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.

Design, synthesis and biological evaluation of 2-phenylquinoline-4-carboxamide derivatives as a new class of tubulin polymerization inhibitors

A novel series of 2-phenylquinoline-4-carboxamide derivatives was synthesized, characterized and evaluated for its antiproliferative activity against five cancer cell lines, Hela, SK-OV-3, HCT116, A549 and MDA-MB-468, and a normal human fetal lung fibroblastic cell line, MRC-5. Among them, compound 7b displayed potent cytotoxic activity in vitro against SK-OV-3 and HCT116 cell lines with IC50 values of 0.5 and 0.2 μM, respectively. In general, the antiproliferative activity was correlated with the binding property of the colchicine binding site and inhibitory effect on tubulin polymerization. In addition, immunofluorescence and flow cytometry analysis revealed that selected compounds caused disruption of the mitotic spindle assembly and G2/M phase arrest of the cell cycle, which correlated with proliferation inhibitory activity. Molecular docking analysis demonstrated the interaction of 7b at the colchicine binding site of tubulin. These results indicate these compounds are promising inhibitors of tubulin polymerization for the potent treatment of cancer.

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

A set of novel quinolone–triazole conjugates (12–31) were synthesized in three steps in good yields starting from 2-phenylquinoline-4-carboxylic acid. All the intermediates, as well as the final 1,2,4-triazolyl quinolines were fully characterized by their detailed spectral analysis utilizing different techniques such as IR, 1H NMR, 13C NMR, and finally mass spectrometry. All the synthesized compounds were evaluated in vitro for their potential antibacterial activity and their preliminary safety profile was assessed through cytotoxicity assay. Additionally, six selected conjugates were evaluated for their antioxidative properties on the basis of density functional theory calculations, using radical scavenging assay (DPPH) and cellular antioxidant assay. The reported results encourage further investigation of selected compounds and are shading light on their potential pharmacological use.

Design, synthesis and antitumour activity of bisquinoline derivatives connected by 4-oxy-3-fluoroaniline moiety

A series of novel bisquinoline derivatives connected by a 4-oxy-3-fluoroaniline moiety were synthesized and evaluated for their in vitro antitumour activities against a panel of five cancer cell lines (H460, HT-29, MKN-45, U87MG, and SMMC-7721). Most of compounds tested showed a potent activity and high selectivity towards the H460 and MKN-45 cell lines. Among the compounds tested, six (15d, 15e, 15m, 15n, 16a, and 16i) were further examined for their c-Met kinase activity; the compounds showed high efficacy with IC 50 values in the single-digit nM range. An analysis of structure-activity relationships indicated that an unsubstituted or a halogen-substituted phenyl ring on the 2-arylquinoline-4-carboxamide moiety was favourable for antitumour activity.

STAT3 INHIBITOR CONTAINING QUINOLINECARBOXAMIDE DERIVATIVE AS ACTIVE INGREDIENT

The present invention provides a STAT3 inhibitor containing as an active ingredient, a quinolinecarboxamide derivative represented by the formula (I) (in the formula, W represents a bond or an alkylene chain; X represents O, S, or NR34; and Rs

Microwave-assisted Doebner synthesis of 2-phenylquinoline-4-carboxylic acids and their antiparasitic activities

(Chemical Equation Presented) A series of twelve substituted 2-phenylquinoline-4-carboxylic acids analogous to antimalarial and antileishmanial natural products was developed via the Doebner reaction employing microwave irradiation (MW). The products were obtained in moderate yields in 0.5-3 minutes and nine of them were evaluated in vitro against the parasites responsible for malaria, leishmaniasis and trypanosomiasis diseases (WHO, Switzerland). Four compounds exhibited activity against Trypanosoma cruzi and another two resulted active against Plasmodium falciparum and Leishmania infantum, respectively.

Synthesis and analgesic-anti-inflammatory activity of certain fluorinated cinchophen analoques

The synthesis of certain fluorinated cinchophen analogues has been achieved.All compounds show analgesic and apparent anti-inflammatory activity comparable to cinchophen and indomethacin but they are toxic at, or close to the 'active' doses.The structure-activity relationship is discussed.