18706-64-4

Basic information

• Product Name: 4-HYDROXY-6-PHENYL-2H-PYRANO[3,2-C]QUINOLINE-2,5(6H)-DIONE
• Synonyms: 4-HYDROXY-6-PHENYL-2H-PYRANO[3,2-C]QUINOLINE-2,5(6H)-DIONE;AURORA KA-2513;4-hydroxy-6-phenylpyrano[3,2-c]quinoline-2,5-dione
• CAS NO: 18706-64-4
• Molecular Formula: C₁₈H₁₁NO₄
• Molecular Weight: 305.28
• Mol File: 18706-64-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 570.7°C at 760 mmHg
• Flash Point: 298.9°C
• Appearance: /
• Density: 1.52g/cm³
• Vapor Pressure: 7.33E-14mmHg at 25°C
• Refractive Index: 1.748
• CAS DataBase Reference: 4-HYDROXY-6-PHENYL-2H-PYRANO[3,2-C]QUINOLINE-2,5(6H)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-6-PHENYL-2H-PYRANO[3,2-C]QUINOLINE-2,5(6H)-DIONE(18706-64-4)
• EPA Substance Registry System: 4-HYDROXY-6-PHENYL-2H-PYRANO[3,2-C]QUINOLINE-2,5(6H)-DIONE(18706-64-4)

Safety Data

• Hazardous Substances Data: 18706-64-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H11NO4/c20-14-10-15(21)23-17-12-8-4-5-9-13(12)19(18(22)16(14)17)11-6-2-1-3-7-11/h1-10,21H

Upstream product

• 71509-17-6 3-(4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-quinolin-3-yl)-3-oxo-propionic acid ethyl ester 
• 122-39-4 diphenylamine 
• 105-53-3 diethyl malonate 
• 52994-51-1 bis-2,4-dichlorophenyl malonate 
• 106993-46-8 N⁽¹⁾,N⁽¹⁾,N⁽³⁾,N⁽³⁾-tetraphenylmalonamide 

Downstream Products

• 141945-46-2 3-nitro-1-phenyl-4-triphenylphosphoranylidene-2(1H)-quinolone 
• 141945-53-1 4-benzylamino-1-phenyl-3-nitro-2(1H)-quinolone 
• 141945-69-9 1-phenyl-3,4-diphenylthio-2(1H)-quinolone 
• 141945-57-5 1-phenyl-4-phenylamino-3-nitro-2(1H)-quinolone 
• 141945-66-6 3-nitro-1-phenyl-4-phenylthio-2(1H)-quinolone 
• 141945-63-3 3-nitro-4-phenoxy-1-phenyl-2(1H)-quinolone 
• 141945-43-9 4-oxo-5-phenyl-4,5-dihydro-1,2,5-oxadiazolo<3,4-c>quinolin 3-oxide 
• 141945-60-0 4-methoxy-3-nitro-1-phenyl-2(1H)-quinolone 

Relevant articles and documents

Synthesis and biological evaluation of some novel hetroaryl quinolinone derivatives

The aim of this study involves the synthesis of novel heterocyclic scaffolds containing quinoline moiety and studying their role as antimicrobial agents. 4-hydroxy-6-phenyl-2H-pyrano[3,2-c]quinoline-2,5(6H))-dione (1) was utilized as a precursor for the construction of new polyheterocyclic ring systems. It reacted with three aryl and (heteroaryl) aldehydes to furnish the corresponding arylidenes 2a-c. The nucleophilic cyclization of compound 2 with hydrazine hydrate to give pyrazolyl quinolinone 3. Moreover, the reaction of 1 with HCHO/morpholine led to the formation of the adduct 7. The synthesized N-(5–3-formyl-4-hydroxy-6-phenyl-2,5-dioxo-5,6-dihydro-2H-pyrano [3,2-c] quinoline (10) was utilized for the synthesis of 3-(([aryl]amino)methylene)-6-phenyl-2H-pyrano[3,2-c]quinoline-2,4,5 (3H,6H)-trione 11a-c via its treatment with three types of amines. Treatment of 1 with POCl3/Et3N afforded the corresponding 4-chloro derivative 20. Which upon treatment with thiourea lead to the formation of the corresponding 4-mercapto derivative 21. The latter 21 was alkylated using ethylbromo acetate giving 22. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses. The synthesized scaffolds were screened for antimicrobial activities also showed promising results. The p-chlorobenzylidene pyrazolylquinolone derivative 3 has excellent antimicrobial properties against Proteus vulgaris compared to its mild activity against Staph aureus. While 4-Chloro-6-phenyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione (20) exhibited good activates against Staph aureus surpassing the activity of reference antibiotic. Also, compounds 21 showed excellent antifungal activity against Candida albicans higher than fluconazole.

Chemistry and pharmacology of pyran derivatives. XII. Derivatives of 2H-pyrano[3,2-c]quinoline

-