36949-55-0

Basic information

• Product Name: 2-hydroxy-1-methyl-3-nitroquinolin-4(1H)-one
• Synonyms: 4-hydroxy-1-methyl-3-nitroquinolin-2(1H)-one;2-hydroxy-1-methyl-3-nitro-1,4-dihydroquinolin-4-one
• CAS NO: 36949-55-0
• Molecular Formula: C₁₀H₈N₂O₄
• Molecular Weight: 220.1815
• Mol File: 36949-55-0.mol

Chemical Properties

• Boiling Point: 303.3°C at 760 mmHg
• Flash Point: 137.2°C
• Density: 1.53g/cm³
• Vapor Pressure: 0.000414mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 2-hydroxy-1-methyl-3-nitroquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-1-methyl-3-nitroquinolin-4(1H)-one(36949-55-0)
• EPA Substance Registry System: 2-hydroxy-1-methyl-3-nitroquinolin-4(1H)-one(36949-55-0)

Safety Data

• Hazardous Substances Data: 36949-55-0(Hazardous Substances Data)

Upstream product

• 626-35-7 nitroacetic acid ethyl ester 
• 10328-92-4 N-Methylisatoic anhydride 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 

Downstream Products

• 1375313-74-8 3-(11-(1H-benzo[d][1,2,3]triazol-1-yloxy)undecanamido)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl 4-methylbenzenesulfonate 
• 1309362-11-5 C₁₇H₁₃FN₂O₃ 
• 1309362-10-4 C₂₀H₂₀N₂O₆ 
• 1309362-07-9 C₂₄H₂₂N₂O₈S₂ 
• 1309362-05-7 C₂₉H₂₆N₂O₆S 
• 1309362-04-6 C₂₉H₂₈N₂O₆S 
• 1309362-02-4 C₂₁H₂₂N₂O₅S 
• 1309362-01-3 C₂₆H₂₁N₃O₅S 
• 1309362-00-2 C₂₂H₁₈N₂O₅S₂ 

Relevant articles and documents

Synthesis of 3H-pyrrolo[2,3-c]quinolin-4(5H)-ones via Pd-catalyzed cross-coupling reaction and cyclization

Biologically active 3H-pyrrolo[2,3-c]quinolin-4(5H)-ones have been synthesized in an efficient and concise manner utilizing readily available 4-hydroxyquinolin-2(1H)-ones as the starting material. The key strategy relies on the construction of the pyrrole ring through the palladium catalyzed sequential cross-coupling reaction and cyclization process.

Synthesis and antikinetoplastid activities of 3-substituted quinolinones derivatives

A new family of quinolinone derivatives has been synthesized and evaluated for their antikinetoplastid activities against Leishmania donovani and Trypanosoma brucei brucei. Results from these structure-activity relationship studies enabled identification of compounds 3a and 4g as the most active compounds against L. donovani promastigotes and amastigotes parasites (IC 50 values in a range of 2-11 μM). Additionally, compound 3b has emerged from this study as the most active compound in the series against T. b. brucei with a MEC value of 12 μM. These three compounds are worth of further in vivo evaluation.

Discovery and biological activity of 6BrCaQ as an inhibitor of the Hsp90 protein folding machinery

Heat shock protein90 (Hsp90) is a significant target in the development of rational cancer therapy, due to its role at the crossroads of multiple signaling pathways associated with cell proliferation and viability. Here, a novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and evaluated in cell proliferation assays. Results from these structure-activity relationships studies enabled identification of the simplified 3-aminoquinolein-2-one analogue 2b (6BrCaQ), which manifests micromolar activity against a panel of cancer cell lines. The molecular signature of Hsp90 inhibition was assessed by depletion of standard known Hsp90 client proteins. Finally, processing and activation of caspases 7, 8, and 9, and the subsequent cleavage of PARP by 6BrCaQ, suggest stimulation of apoptosis through both extrinsic and intrinsic pathways. Hot stuff! A novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and screened in cell proliferation assays. The most potent inhibitor, 6BrCaQ, exhibited strong antiproliferative activity against a panel of cancer cell lines and resulted in downregulation of Hsp90 client proteins. Moreover, 6BrCaQ induced a high level of apoptosis in MCF-7 breast cancer cells, and was found to mediate cell death in a p23-independent manner.

Inhibitors of macrophage migration inhibitory factor and methods for identifying the same

Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R1, R2, R3, R4, X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

SPIROCYCLIC MEISENHEIMER COMPLEXES. XXXV. POSSIBLE FORMATION OF ANIONIC SPIRO ? COMPLEXES IN THE 3-NITRO-2(1H)-QUINOLINONE SYSTEM

The reaction of 1-methyl-3-nitro- and 1-methyl-3,6-dinitro-4-chloro-2(1H)-quinolinones with 1,2-ethanedithiol leads to 1-methyl-3-nitro- and 1-methyl-3,6-dinitrospirodithiolanes>.The ability of the latter to form anionic Meisenheimer spiro ? complexes is less than in the analogous derivatives of benzopyranone and benzothiopyranone.

Nucleophilic Substitution and Ring Closure Reactions of 4-Chloro-3-nitro-2-quinolones

4-Chloro-3-nitro-2-quinolones 3 obtained from the 4-hydroxy quinolones 1 by nitration and chlorination, reacted with sodium azide to the 4-azido derivatives 4 which cyclized on thermolysis to yield the furoxanes 5.Nucleophilic substitution reactions of 3

Chemistry of Carbostyril: Part I - Oxidation Reactions of 4-Hydroxy- and 4-Hydroxy-1-methyl-2(1H)-quinolinones

4-Hydroxy-2(1H)-quinolinone (1) reacts with acetic anhydride in dimethylsulphoxide at 100 deg to afford 3-dimethylsulfonioquinoline-2,4-dionate (3) whereas 3,3'-methylenebis (4) and 2,3,4,5,1',2',3',4'-octahydro-4,2',4'-trioxospioroquinoline-2,3'-quinoline> (5) are formed when the reaction is carried out at 165-70 deg.The involvement of 4 as a precursor of 5 has been demonstrated.Probable mechanisms of their formation have been proposed.The behaviour of 4-hydroxy-1-methyl-2(1H)-quinolinone (2) towards other oxidising agents, such as HNO3, CrO3, SOCl2-DMF and p-benzoquinone has also been studied.

4-Hydroxy-3-nitro-quinoline-2(1H)-ones

Anti-allergic 4-hydroxy-3-nitro-quinoline-2(1H)-ones are prepared by reacting an isatoic anhydride with the carbanion resulting from the treatment of nitro acetic acid alkyl esters with a proton abstracting agent.

Anti-allergenic carbostyril derivatives

A class of 4-hydroxy-3-nitroearbostyril derivatives are useful in the inhibition of certain types of antigen antibody reactions.