1873-59-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-3-methyl-4-quinolone is used as a pharmaceutical agent for its potential antibacterial and antifungal properties, offering a new avenue for the development of antimicrobial drugs to combat resistant strains.
Used in Chelating Agents:
In the field of chemistry, 2-hydroxy-3-methyl-4-quinolone is used as a chelating agent for metal complexation, which can be beneficial in various chemical processes and applications where metal ion management is required.
Used in Antioxidant Applications:
2-Hydroxy-3-methyl-4-quinolone is utilized as an antioxidant, which can be incorporated into formulations to prevent oxidative damage in various industrial and biological systems, including pharmaceuticals and cosmetics.
Used in Medicinal Chemistry Research:
As a compound of interest in medicinal chemistry, 2-hydroxy-3-methyl-4-quinolone is used in research to explore its potential therapeutic applications and to understand its mechanisms of action, which could lead to the development of new drugs and therapies.

InChI:InChI=1/C10H9NO2/c1-6-9(12)7-4-2-3-5-8(7)11-10(6)13/h2-5H,1H3,(H2,11,12,13)

Upstream product

• 609-08-5 Diethyl methylmalonate 
• 87-25-2 2-ethoxycarbonylaniline 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 1264-45-5 (2RS)-methylmalonyl-CoA 
• 62-53-3 aniline 
• 52629-26-2 ethyl 2-(N-phenylcarbamoyl)propanoate 
• 6833-01-8 Methylmalonsaeure-dianilid 
• 67-56-1 methanol 
• 773837-37-9 sodium cyanide 
• 144603-20-3 3-chloro-3-methylquinoline-2,4(1H,3H)-dione 
• 1399323-75-1 1,2,3,4-tetrahydro-3-methyl-2,4-dioxoquinolin-3-yl thiocyanate 
• 15601-92-0 2-methyl-3-oxo-3-(phenylamino)propanoic acid 
• 529-89-5 4-hydroxy-3-formyl-1H-quinolin-2-one 
• 862255-44-5 2-carboethoxyanilide monoethyl ester of methylmalonic acid 

Downstream Products

• 14469-11-5 2-[(2-oxopropanoyl)amino]benzoic acid 
• 523-64-8 flindersine 
• 873399-47-4 (4-chloro-3-methyl-[2]quinolyl)-(4-chloro-phenyl)-amine 
• 56857-97-7 2,4-dichloro-3-methyl-quinoline 

Relevant academic research and scientific papers

Synthesis of intervenolin, an antitumor natural quinolone with unusual substituents

Synthesis of intervenolin, a natural quinolone discovered by screening for selective growth inhibitors of cancer cells cocultured with stromal cells over monocultured cells, was achieved. The synthesis utilized a thiocyanate- isothiocyanate rearrangement and Suzuki-Miyaura coupling to furnish the characteristic substituents, the iminodithiocarbonate moiety, and the geranyl side chain, respectively. In vivo studies showed that intervenolin inhibited tumor tissue growth in model mice.

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones

3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position

4-Hydroxy-3-methyl-2(1h)-quinolone, originally discovered from a brassicaceae plant, produced by a soil bacterium of the genus burkholderia sp.: Determination of a preferred tautomer and antioxidant activity

4-Hydroxy-3-methyl-2(1H)-quinolone (1), a molecule known for a long time and recently discovered from a Brassicaceae plant Isatis tinctoria without providing sufficient evidence to support the structure, was isolated from a fermentation extract of Burkholderia sp. 3Y-MMP isolated from a soil by a Zn2+ enrichment culture. Detailed spectroscopic analyses by MS and NMR, combined with 13C chemical shift comparison with literature values of the related compounds and a synthetic preparation of 1, allowed its first full NMR characterization and identification of 2-quinolone but not 2-quinolinol (2) as the preferred tautomer for this heterocyclic system. While the metal-chelating activity was negligible, compound 1 at 10 μM, a concentration lower than that in liquid production cultures, quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86percent. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response in the host organisms.

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday

N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is

Modified riemschneider reaction of 3-thiocyanatoquinolinediones

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright

HETEROCYCLIC COMPOUNDS AND THEIR USES

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjogren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110δ activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.

Enzymatic formation of quinolone alkaloids by a plant type III polyketide synthase

(Chemical Equation Presented) Benzalacetone synthase from Rheum palmatum efficiently catalyzed condensation of N-methylanthraniloyl-CoA (or anthraniloyl-CoA) with malonyl-CoA (or methylmalonyl-CoA) to produce 4-hydroxy-2(1H)-quinolones, a novel alkaloidal scaffold produced by a type III polyketide synthase (PKS). Manipulation of the functionally divergent type III PKSs by a nonphysiological substrate thus provides an efficient method for production of pharmaceutically important quinolone alkaloids.

4-HYDROXY-2-QUINOLONES 19. A NEW SYNTHESIS OF 3-ALKYL-2-OXO-4-HYDROXYQUINOLINES

3-Alkyl-subtituted 2-oxo-4-hydroxyquinolines were obtained in high yields from N,N'-di-2-alkoxycarbonylanilides of alkylmalonic acids under conditions of the Dieckmann condensation.Some types of biological activity were found for the compounds synthesized.