634-38-8

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-QUINOLINE-4-CARBOXYLIC ACID is used as a key intermediate in the synthesis of dihydro pyrano pyrazolone derivatives, which are known for their antitumor properties. These derivatives have the potential to target and inhibit the growth of cancer cells, making them valuable in the development of novel cancer therapies.
2-METHYL-QUINOLINE-4-CARBOXYLIC ACID is used as a building block for the preparation of various pharmaceutical compounds, due to its unique chemical structure and reactivity. This allows for the creation of new drug candidates with potential therapeutic benefits in treating cancer and other diseases.

InChI:InChI=1/C11H9NO2/c1-7-6-9(11(13)14)8-4-2-3-5-10(8)12-7/h2-6H,1H3,(H,13,14)

Upstream product

• 91-56-5 indole-2,3-dione 
• 127-17-3 2-oxo-propionic acid 
• 62-53-3 aniline 
• 103-70-8 Formanilid 
• 67-64-1 acetone 
• 33417-17-3 3-hydroxy-3-(2-oxopropyl)indolin-2-one 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 15226-74-1 dicobalt octacarbonyl 
• 123172-90-7 2-methylquinolin-4-yl trifluoromethanesulfonate 
• 142-04-1 aniline hydrochloride 
• 75-07-0 acetaldehyde 
• 15821-13-3 2-methylquinoline-4-carboxamide 
• 1198-37-4 2,4-dimethylquinoline 

Downstream Products

• 55625-40-6 methyl 2-methylquinoline-4-carboxylate 
• 91-63-4 2-methylquinoline 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 15821-13-3 2-methylquinoline-4-carboxamide 
• 7120-26-5 ethyl 2-methylquinoline-4-carboxylate 
• 90673-26-0 pyridine-2,3,4,6-tetracarboxylic acid 
• 5774-31-2 nitrofuran IIIa 
• 73418-22-1 benzyl-[5-(2-methyl-quinolin-4-yl)-[1,3,4]thiadiazol-2-yl]-amine 
• 73418-25-4 (2-methoxy-phenyl)-[5-(2-methyl-quinolin-4-yl)-[1,3,4]thiadiazol-2-yl]-amine 
• 64819-75-6 4-benzooxazol-2-yl-2-methyl-quinoline 
• 73418-23-2 [5-(2-methyl-quinolin-4-yl)-[1,3,4]thiadiazol-2-yl]-phenyl-amine 
• 73418-24-3 [5-(2-methyl-quinolin-4-yl)-[1,3,4]thiadiazol-2-yl]-o-tolyl-amine 
• 31432-65-2 C₁₈H₁₂N₂O₅ 
• 118967-32-1 2-styrylquinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Study on synthesis and fluorescence property of rhodamine–naphthalene conjugate

In this study, a novel ligand (HL) consisting of 2-methyl quinoline-4-carboxylic acid, rhodamine and naphthalene moiety, was designed and synthesized, it could be developed a ratiometric fluorescent sensor for selective detection of Al3+ via fluorescence resonance energy transfer (FRET) from naphthalimide moiety to rhodamine moiety. The addition of Al3+ trigger the significant fluorescence enhancement of HL at 550 nm at the expense of the fluorescent emission of HL centered at 524 nm.

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.

Quinoline substituted chalcone compound as well as preparation method and application thereof

The invention discloses a novel quinoline substituted chalcone compound as well as pharmaceutically acceptable salts and a preparation method thereof. The invention further discloses a pharmaceuticalcomposition which comprises a therapeutically effective amount of the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts and a pharmaceutically acceptable carrier. The invention further discloses a tubulin inhibitor which comprises the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts. The invention further disclosesapplication of the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts in preparing drugs for treating but not limited to colon cancer, leukemia, liver cancer, breast cancer and other diseases. The compound in the application shows excellent anti-tumor activity, and has more stable metabolic properties and better druggability prospect.

Discovery of Novel Quinoline-Chalcone Derivatives as Potent Antitumor Agents with Microtubule Polymerization Inhibitory Activity

A series of novel quinoline-chalcone derivatives were designed, synthesized, and evaluated for their antiproliferative activity. Among them, compound 24d exhibited the most potent activity with IC50 values ranging from 0.009 to 0.016 μM in a panel of cancer cell lines. Compound 24d also displayed a good safety profile with an LD50 value of 665.62 mg/kg by intravenous injection, and its hydrochloride salt 24d-HCl significantly inhibited tumor growth in H22 xenograft models without observable toxic effects, which was more potent than that of CA-4. Mechanism studies demonstrated that 24d bound to the colchicine site of tubulin, arrested the cell cycle at the G2/M phase, induced apoptosis, depolarized mitochondria, and induced reactive oxidative stress generation in K562 cells. Moreover, 24d has potent in vitro antimetastasis and in vitro and in vivo antivascular activities. Collectively, our findings suggest that 24d deserves to be further investigated as a potent and safe antitumor agent for cancer therapy.

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.

Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl

An efficient method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co2(CO)8] has been developed. Besides acting as carbon monoxide (CO) source, Co2(CO)8enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd-Co(CO)4] complex. Under the optimized reaction condition, carbonylation of a wide range of activated and deactivated, as well as sterically hindered and heteroaromatic, substrates proceeded efficiently at room temperature. The high chemoselectivity and improved synthesis of biologically relevant Isoguvacine and Lazabemide intermediates highlights its scope as a valuable synthetic method. The generality of this protocol was further extended to other electrophiles (bromides, chlorides and tosylates). (Figure presented.).

Microwave-assisted synthesis of 2-styrylquinoline-4-carboxylic acids as antitubercular agents

Background: Many 2-substituted quinolines and especially 2-arylvinyl derivatives isolated from plants or prepared by synthesis have been designed from ethnopharmacological studies. Objective: In order to explore new aspects of the structure-antituberculos

Convergent synthesis and cytotoxicity of novel trifluoromethyl-substituted (1H-pyrazol-1-yl)(quinolin-4-yl) methanones

A convergent synthesis of a series of 16 new polysubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)(quinolin-4-yl)methanones, starting from isatin and alky(aryl/heteroaryl) ketones, is described. The diheteroaryl methanones were achieved at yields of up to 95% by a [3?+?2] cyclocondensation reaction involving 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluorobut-3-en-2-ones (by two-step reaction) and 2-alkyl(aryl/heteroaryl)-4-carbohydrazides (by three-step reaction). Subsequently, representative dehydrated heterocyclic derivatives were obtained from the respective 5-hydroxy-2-pyrazoline moieties by classical dehydration reactions, which resulted in the corresponding (5-(trifluoromethyl)-1H-pyrazol-1-yl)(quinolin-4-yl)methanones (three examples) at yields of 69–82%. The subsequent cytotoxicity evaluation showed that compounds with aromatic groups at the 2-position of the quinoline and a methyl moiety at the 3-position of the pyrazole have significant cytotoxicity in human leukocytes at high concentrations (200?μM).

Fluorescent sensor for selective detection of Al3+ based on quinoline-coumarin conjugate

A fluorescence probe, 8-formyl-7-hydroxyl-4-methyl coumarin - (2′-methylquinoline-4-formyl) hydrazone (L) has been synthesized. The chemosensor is found preferential binding to Al3+ in presence of other competitive ions with associated changes in its optical and fluorescence spectra behavior. Upon addition of Al3+ to a solution of L, it shows 200-fold enhancement of fluorescence intensity which might be attributed to form a 2:1 stoichiometry of the binding mode of LAl(III) and the chelation enhanced fluorescence (CHEF) process at 479 nm in ethanol. The lowest detection limit for Al3+ is determined as 8.2 × 10-7 M.

Discovery of novel small molecule inhibitors of dengue viral NS2B-NS3 protease using virtual screening and scaffold hopping

By virtual screening, compound 1 was found to be active against NS2B-NS3 protease (IC50 = 13.12 ± 1.03 μM). Fourteen derivatives (22) of compound 1 were synthesized, leading to the discovery of four new inhibitors with biological activity. In order to expand the chemical diversity of the inhibitors, small-molecule-based scaffold hopping was performed on the basis of the common scaffold of compounds 1 and 22. Twenty-one new compounds (23, 24) containing quinoline (new scaffold) were designed and synthesized. Protease inhibition assays revealed that 12 compounds with the new scaffold are inhibitors of NS2B-NS3 protease. Taken together, 17 new compounds were discovered as NS2B-NS3 protease inhibitors with IC50 values of 7.46 ± 1.15 to 48.59 ± 3.46 μM, and 8 compounds belonging to two different scaffolds are active to some extent against DENV based on luciferase reporter replicon-based assays. These novel chemical entities could serve as lead structures for discovering therapies against DENV.