- Quinolone alkaloids from Evodia rutaecarpa
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Five new quinolone alkaloids were isolated from the fruits of Evodia rutaecarpa, together with seven known ones. Their structures were determined on the basis of spectral data and chemical reactions.
- Tang, Yuan-Qing,Feng, Xiao-Zhang,Huang, Liang
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- Alkylation of pyridone derivatives by nickel/Lewis acid catalysis
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MAD as an additive: The [Ni(cod)2], (2,6-tBu2-4- MeC6H2O)2AlMe (MAD), and N-heterocyclic carbene (NHC) catalytic system effected a highly regioselective alkylation of pyridone derivatives (see scheme). Substituted pyridones and related heterocycles react with both terminal and internal alkenes to selectively give a range of nitrogen-containing heterocycles with linear alkyl substituents. Copyright
- Tamura, Ryuichi,Yamada, Yuuya,Nakao, Yoshiaki,Hiyama, Tamejiro
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supporting information; experimental part
p. 5679 - 5682
(2012/07/14)
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- Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl- 4(1H)-quinolones
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A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships.
- Wube, Abraham A.,Hüfner, Antje,Thomaschitz, Christina,Blunder, Martina,Kollroser, Manfred,Bauer, Rudolf,Bucar, Franz
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p. 567 - 579
(2011/03/17)
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- The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 17. Synthesis of 2-Alkyl-4-quinolone Alkaloids via a One-step Reaction of N-Methylisatoic Anhydride with Methyl Ketone Enolates
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Lithium enolates derived from aliphatic methyl ketones react with N-methylisatoic anhydride (5) at -78 deg C to give 2-alkyl-4-quinolone alkaloids 7 in a single step.The method was used to synthesize both double bond isomers of 1-methyl-2-(8-tridecenyl)-4(1H)-quinolinone (8) thereby showing that the alkaloid evocarpine possesses the Z-olefin stereochemistry 8a.Reduction of 8a provided the alkaloid dihydroevocarpine (16).Compound 16 was also directly prepared from the reaction of 5 with the lithium enolate of 2-pentadecanone.
- Coppola, Gary M.
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p. 491 - 494
(2007/10/02)
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