30674-34-1Relevant academic research and scientific papers
Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives
Kusakabe, Yasuha,Mizutani, Shoma,Kamo, Shogo,Yoshimoto, Tatsuki,Tomoshige, Shusuke,Kawasaki, Tsuneomi,Takasawa, Ryoko,Tsubaki, Kazunori,Kuramochi, Kouji
, p. 1390 - 1394 (2019/04/01)
The antibacterial and cytotoxic activity of seven racemic lactams and both enantiomers of flavipucine were evaluated. Of the compounds tested in this study, flavipucine and phenylflavipucine displayed bactericidal activity against Bacillus subtilis. These
A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine
Mizutani, Shoma,Komori, Kenta,Taniguchi, Tohru,Monde, Kenji,Kuramochi, Kouji,Tsubaki, Kazunori
, p. 9553 - 9556 (2016/08/10)
A biomimetic synthesis of naturally occurring lactams rubrobramide, flavipucine, and isoflavipucine is described. The key step is a regioselective Darzens reaction between isobutyl glyoxal and an α-bromo-β-ketoamide. The construction of the core tricyclic ring system of rubrobramide was achieved by a cascade reaction in a single step from an α,β-epoxy-γ-lactam. Furthermore, the absolute configuration of naturally occurring (+)-rubrobramide was determined by vibrational circular dichroism. (±)-Flavipucine and (±)-isoflavipucine were synthesized from an epoxyimide, which was prepared by reaction of isobutyl glyoxal with a protected α-bromo-β-ketoamide. Deprotection of the epoxyimide and formation of the pyridone ring gave (±)-flavipucine, which was converted into (±)-isoflavipucine by thermal isomerization.
Synthesis and Biological of Flavipucine Analogues
Girotra, N. N.,Patchett, A. A.,Zimmerman, S. B.,Achimov, D. L.,Wendler, N. L.
, p. 209 - 213 (2007/10/02)
A series of analogues of flavipucine was prepared possessing side chain as well as nuclear variants.The analogue with an octyl side chain (5d) was found to exhibit enhanced activity against several bacteria and fungi as compared with the natural product i
Chemical synthesis of flavipucine
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, (2008/06/13)
A method for the total chemical synthesis of flavipucine employs the condensation of 4-hydroxy-6-methyl-2-pyridone with isobutylglyoxal in alkali alkoxide. The resulting alkali salt is acylated in both the 1' and 4 positions. Treatment of the 1',4-diacyloxy derivative with excess alkaline peroxide yields flavipucine.
