26138-64-7

Usage

Uses

Used in Pharmaceutical Applications:
3-acetyl-4-hydroxy-2-quinolone is used as an active pharmaceutical ingredient for its antibiotic and antifungal properties, serving to combat a range of microbial infections. Its broad-spectrum activity makes it a valuable asset in the development of new antimicrobial agents.
Used in Cancer Therapy Research:
In the field of oncology, 3-acetyl-4-hydroxy-2-quinolone is used as a potential therapeutic agent for cancer treatment. Studies have indicated its capacity to inhibit tumor growth, making it a subject of interest for further research and development in cancer therapies.
Used in Drug Development:
3-acetyl-4-hydroxy-2-quinolone's multifaceted biological activities position 3-acetyl-4-hydroxy-2-quinolone as a key player in drug development. Its potential to be formulated into various pharmaceutical products highlights its use as a precursor or building block in the creation of novel medicines targeting infectious diseases and cancer.

InChI:InChI=1/C11H9NO3/c1-6(13)9-10(14)7-4-2-3-5-8(7)12-11(9)15/h2-5H,1H3,(H2,12,14,15)

Upstream product

• 70254-44-3 2,4-dihydroxyquinoline 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 570-08-1 diethyl acetylmalonate 
• 62-53-3 aniline 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 86119-84-8 phosphoric acid 
• 81937-41-9 Methyl N-acetoacetylanthranilate 
• 41470-88-6 2-ethoxy-4H-benzo[d][1,3]oxazin-4-one 
• 89-52-1 o-acetylamino-benzoic acid 
• 141-97-9 ethyl acetoacetate 
• 134-20-3 2-carbomethoxyaniline 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 118-92-3 anthranilic acid 

Downstream Products

• 1478449-20-5 C₁₉H₁₆N₂O₃ 
• 4694-51-3 7-methyldibenzo[c,f][2,7]naphthyridin-6(5H)-one 
• 1478449-16-9 3-(1-(phenylimino)ethyl)-2,4-dihydroxyquinoline 
• 1478449-56-7 3-(1-(4-methylphenylimino)ethyl)-2,4-dihydroxyquinoline 
• 1478449-58-9 3-(1-(2-methoxyphenylimino)ethyl)-2,4-dihydroxyquinoline 
• 1478449-60-3 3-(1-(4-methoxyphenylimino)ethyl)-2,4-dihydroxyquinoline 
• 54289-76-8 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone 
• 101569-81-7 4-hydroxy-3-[1-(phenylhydrazono)ethyl]-quinolin-2(1H)-one 
• 1190695-30-7 C₂₇H₂₆N₄O₅ 
• 1333500-29-0 C₁₉H₁₅NO₅ 
• 1333500-25-6 C₁₈H₁₂FNO₃ 
• 163232-53-9 C₁₈H₁₂ClNO₃ 
• 1333500-26-7 4-hydroxy-3-[3-(4-nitrophenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone 

Relevant academic research and scientific papers

Novel quinolinone–pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity

Abstract: The present project deals with the investigation of structure–activity relationship of several quinolinone–chalcone and quinolinone–pyrazoline hybrids, in an effort to discover promising antioxidant and anti-inflammatory agents. In order to accomplish this goal, four bioactive hybrid quinolinone–chalcone compounds (8a–8d) were synthesized via an aldol condensation reaction, which were then chemically modified, forming fifteen new pyrazoline analogues (9a–9o). All the synthesized analogues were in vitro evaluated in terms of their antioxidant and soybean lipoxygenase (LOX) inhibitory activity. Among all the pyrazoline derivatives, compounds 9b and 9m were found to possess the best combined activity, whereas 9b analogue exhibited the most potent LOX inhibitory activity, with IC50 value 10?μM. The in silico docking results revealed that the synthetic pyrazoline analogue 9b showed high AutoDock Vina score (? 10.3?kcal/mol), while all the tested derivatives presented allosteric interactions with the enzyme. Graphic Abstract: [Figure not available: see fulltext.]

Novel 'quinolone' metal complexes: Synthesis and spectroscopic studies of Mg(II), Zn(II) and Ba(II) complexes with N-methyl (or NH)-3-acetyl-4-hydroxy quinolin-2-one ligands

The complexation between N-methyl-3-acetyl-4-hydroxyquinolin-2-one (NMeQuin) and N-H-3-acetyl-4-hydroxy quinolin-2-one (NHQuin) with MgCl 2, ZnCl2 and BaCl2 has been accomplished. The structure of the resulting complexes 1-5 has been elucidated through elemental analyses, FT-IR and 1H/13C NMR Spectroscopy and Mass Spectrometry. The spectroscopic data show complexes of the general formula Mg2(OH)L3(H2O)z and ML 2(H2O)z where: M = Zn(II) and Ba(II), L = NMeQuin, NHQuin and z = 2,4.

Synthesis, antioxidant and toxicological study of novel pyrimido quinoline derivatives from 4-hydroxy-3-acyl quinolin-2-one

A series of novel pyrimido and other fused quinoline derivatives like 4-methyl pyrimido [5,4-c]quinoline-2,5(1H,6H)-dione (4a), 4-methyl-2-thioxo-1,2- dihydropyrimido [5,4-c]quinoline-5(6H)-one (4b), 2-amino-4-methyl-1,2- dihydropyrimido [5,4-c]quinolin-5(6H)-one (4c), 3-methylisoxazolo [4,5-c]quinolin-4(5H)-one (4d), 3-methyl-1H-pyrazolo [4,3-c]quinoline-4(5H)-one (5e), 5-methyl-1H-[1,2,4] triazepino [6,5-c]quinoline-2,6(3H,7H)-dione (5f), 5-methyl-2-thioxo-2,3-dihydro-1H-[1,2,4]triazepino [6,5-c]quinolin-6(7H)-one (5g) were synthesized regioselectively from 4-hydroxy-3-acyl quinolin-2-one 3. They were screened for their in vitro antioxidant activities against radical scavenging capacity using DPPH, Trolox equivalent antioxidant capacity (TEAC), total antioxidant activity by FRAP, superoxide radical (O2°-) scavenging activity, metal chelating activity and nitric oxide scavenging activity. Among the compounds screened, 4c and 5g exhibited significant antioxidant activities.

Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins

Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-2H-chromen-2-one; BHC) was previously discovered to inhibit skeletal myosin II. BHC and 34 analogues were synthesized to explore structure-activity relationships. The properties of analogues, including solubility, stability, and toxicity, suggest that the BHC scaffold may be useful for developing therapeutics. Inhibition of actin-activated ATPase activity of fast skeletal and cardiac muscle myosin II, inhibition of skeletal muscle contractility ex vivo, and slowing of in vitro actin-sliding velocity were measured. Several analogues with aromatic side arms showed improved potency (half-maximal inhibitory concentration (IC50) 1 μM) and selectivity (≥12-fold) for skeletal myosin versus cardiac myosin compared to BHC. Several analogues blocked neurotransmission, suggesting that they are selective for nonmuscle myosin II over skeletal myosin. Competition and molecular docking studies suggest that BHC and blebbistatin bind to the same site on myosin.

Structure of the imine 4-hydroxy-2-quinoline ketone compound, and its preparation and use

The invention relates to 4-hydroxy-2-quinolinone compounds containing an imine structure, and preparation and an application thereof. A general formula is represented as the formula (I), wherein meanings of groups in the formula are defined in the specification. The compounds represented by the general formula (I) have quite good herbicidal and fungicidal activities and are widely applied in prevention and treatment of weeds and pathogenic bacteria of crops.

Substituted quinolinones. 18. 3-Acetyl-4-methylthioquinolin-2(1H)-one as useful synthon intermediate for synthesis of some new quinolinones

3-Acetyl-4-methylthioquinolin-2(1H)-one (3) has been prepared and its reactivity towards treatment with different reagents, dilute sulfuric acid, aqueous sodium hydroxide, and hydrogen peroxide, is described. The reactions of compound 3 with benzylamine,

Synthesis and anti-parasitic activity of a novel quinolinone-chalcone series

A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 ± 0.1 μM). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 ± 0.6 and 3.1 ± 1.05 μM, respectively). Promising trypanocidal compounds include 5 and 10 (IC 50 values of 2.6 ± 0.1 and 3.3 ± 0.1 μM, respectively) as well as 6 and 9 (both having IC50 values of 5 μM). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity.

Reactivity of 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3- d][1,3]oxazin-4-one under microwave irradiation conditions

The reactivity of variably substituted 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one towards carbon and oxygen nucleophiles under microwave irradiation conditions was investigated. Optimization of the reaction conditions of oxazinones with carbon nucleophiles led to the synthesis of a series of 4-hydroxy-quinolin-2-ones and 4-hydroxy-1,8-naphthyridin-2-ones in high yields, whereas reaction with a variety of alcohols proceeded smoothly to the formation of the corresponding N-acetyl-anthranilates and nicotinates.

A one pot microwave assisted synthesis of 3-acyl-2,4-dihydroxyquinoline followed by synthesis of 7-methyldibenzo[c,f][2,7]naphthyridin-6(5H)-ones via three routes

An easy one pot microwave assisted synthesis of 3-acyl-2,4- dihydroxyquinoline from simple precursors followed by convenient synthesis of novel and potential HIV integrase inhibitors 7-methyldibenzo[c,f][2,7] naphthyridin-6(5H)-ones has been achieved through three different routes. Mild reaction conditions and good yields are obtained by applying microwave and photochemical techniques.

L-Proline as an efficient catalyst for synthesis of N-heterocyclic chalcones as potential antibacterial agents

The condensation of 4-hydroxy-3-acetyl-1H-quinoline-2-one 1 and substitutedbenzaldehydes 2a-i in DMSO solution at room temperature yields quinolone chalcone derivatives 3a-i. L-Proline has been found to be an efficient catalyst for this condensation between 1 and 2. Only 5 mol% of the catalyst is necessary to achieve good yields of the products. Reactions proceed smoothly with variations of the substituents. 1 itself is synthesized by the acylation of commercially available methyl anthranilate 4 with acetoacetic ester 5 in refluxing xylene and subsequent Dieckman intramolcular cyclization of the intermediary 2-methoxycarbonylanilide 6.