64190-94-9

Usage

Uses

Used in Pharmaceutical Industry:
Zanthobungeanine is used as an anti-inflammatory agent for its ability to inhibit interleukin-1β-induced prostaglandin E2 production, which can help in reducing inflammation and pain.
Used in Antimicrobial Applications:
Zanthobungeanine is used as an antimicrobial agent for its activity against different strains of bacteria, which can help in treating bacterial infections.
Used in Anticancer Applications:
Zanthobungeanine is used as an anti-tumor and anti-cancer agent for its potential to inhibit the growth and progression of cancer cells, making it a promising candidate for further research and development of therapeutic applications in oncology.

Upstream product

• 3912-74-1 3,4,5,6-tetrahydro-7-methoxy-2,2,6-trimethyl-5-oxo-2H-pyrano-<3,2-c>-quinoline 
• 74-88-4 methyl iodide 
• 35989-00-5 7-methoxy-2,2-dimethyl-2H,5H,6H-pyran[3,2-c]quinolin-5-one 
• 7224-68-2 4-hydroxy-8-methoxyquinolin-2(1H)-one 
• 3148-27-4 4-hydroxy-8-methoxy-N-methylquinolin-2(1H)-one 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 90-04-0 2-methoxy-phenylamine 
• 4843-06-5 2-(2-methoxyphenyl)carbamoylacetic acid 
• 90475-72-2 2-methoxymalonanilic acid ethyl ester 
• 96838-26-5 4-Hydroxy-8-methoxy-3-[2-methyl-prop-(E)-ylidene]-3H-furo[2,3-b]quinolin-2-one 
• 96838-22-1 6-Methoxy-3-[2-methyl-prop-(Z)-ylidene]-3,5-dihydro-furo[3,2-c]quinoline-2,4-dione 
• 96838-75-4 (Z)-2-(4-Hydroxy-8-methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-4-methyl-pent-2-enoic acid 
• 96838-80-1 4-Hydroxy-8-methoxy-2-quinolone-3-acetic acid 
• 7691-03-4 3-(γ,γ-dimethylallyl)-4-hydroxy-8-methoxy-2-quinolone 

Relevant academic research and scientific papers

Asymmetric Total Synthesis and Biological Evaluation of the Natural PDE4 Inhibitor Toddacoumalone

We describe herein the first asymmetric total synthesis and biological evaluation of the natural PDE4 inhibitor toddacoumalone and its stereoisomers. The key step of the total synthesis is a formal asymmetric [4 + 2] cycloaddition reaction catalyzed by chiral secondary amine catalysts. A variety of pyranoquinolinones and 3-methylcrotonaldehyde are well tolerated under the optimized reaction conditions, which paved the way for further SAR studies. Further biological evaluation showed 1a′ with the best PDE4 inhibitory activity (IC50 = 0.18 μM).

Synthesis of Pyranoquinolin-5-one Alkaloids: Veprisine, 7-Dimethylallyloxy-N-methylflindersine and cis-3,4-Dihydroxy-7-methoxy-2,2,6-trimethyl-3,4,5,6-tetrahydro-2H-pyranoquinolin-5-one

Condensation of the appropriate 4-hydroxyquinolin-2-ones with 3-methylbut-2-enal gave pyranoquinolin-5-ones which were further elaborated to three alkaloids named in the title.

QUINOLINONE ALKALOIDS FROM AN AGATHOSMA SPECIES

The aerial parts of a new species from the genus Agathosma yielded skimmianine and two new alkaloids which were identified by means of spectral data and synthesis as 4,6-dimethoxy-1-methyl-2(1H)-quinolinone and 2,6-dihydro-9-methoxy-2,2,6-trimethyl-5H-pyr

A NEW APPROACH TO HEMITERPENOID TRICYCLIC QUINOLONES. SYNTHESIS OF N-METHYLFLINDERSINE, KHAPLOPHOLINE AND OTHER STRUCTURALLY SIMILAR ALKALOIDS

A new and general synthesis of tricyclic quinolone alkaloids is described which, by cyclization of 3-butenyl-4-hydroxyquinolones promoted by mercury(II) ion or by formic acid, affords pyranoquinolones and pyranoquinolones, respectively, with regio- and site-selectivity better than those obtained employing known methodologies. 3-Butenyl-4-hydroxyquinolones have been reacted with mercury(II) acetate to give, after work-up, the corresponding 2-(chloromercurymethyl)pyranoquinolones, which have been reductively demercurated with sodium borohydride and then dehydrogenated by treatment with DDQ.Alternatively, from the same starting compounds the "linear" isomers are obtained by formic acid-promoted cyclization.N-Methylflindersine, khaplofoline and other structurally similar alkaloids have been obtained.

A CONVENIENT SYNTHESIS OF FLINDERSINE, ATANINE AND THEIR ANALOGUES

A new synthesis of the pyranoquinolone alkaloids flindersine (8a), 8-methoxyflindersine (8c), N-methylflindersine (9a), zanthobunglanine (9c), oricine (9d) and veprisine (9e) and the prenylquinolone alkaloids atanine (13a), preskimmianine (13e), N-methylatanine (14a), O-methylglycosolone (14c) and N-methylpreskimmianine (14e) is described.