Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives.

@article{Kusakabe2019SynthesisAA,
  title={Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives.},
  author={Yasuha Kusakabe and Shoma Mizutani and Shogo Kamo and Tatsuki Yoshimoto and Shusuke Tomoshige and Tsuneomi Kawasaki and Ryoko Takasawa and Kazunori Tsubaki and Kouji Kuramochi},
  journal={Bioorganic \& medicinal chemistry letters},
  year={2019},
  volume={29 11},
  pages={
          1390-1394
        }
}
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References

SHOWING 1-10 OF 23 REFERENCES
(+)‐Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics
From the culture extracts of the endophytic fungus, Phoma sp., isolated from the plant Salsola oppositifolia, five secondary metabolites were isolated and characterized. On biomalt agar medium, the
Synthesis and biological activity of flavipucine analogues.
TLDR
A series of analogues of flavipucine prepared possessing side chain as well as nuclear variants were found to exhibit enhanced activity against several bacteria and fungi as compared with the natural product itself.
Metabolism and pharmacokinetics of the camptothecin analogue CPT-11 in the mouse.
TLDR
In vitro incubation of CPT-11 in mouse serum or tissue homogenate enhanced the growth-inhibitory activity much more than that expected from the concentration of C PT-11, and it is suggested that the maintenance of plasma SN-38 concentration might be necessary for it to exhibit antitumor activity in vivo.
Flavipucine and Brunnescin, Two Antibiotics from Cultures of the Mycophilic Fungus Cladobotryum rubrobrunnescens
TLDR
The metabolite isolated from submerged cultures of Cladobotryum rubrobrunnescens, a mycophilic fungus growing on a Inocybe species, is a new tetrasubstituted furan derivative which exhibits antibacterial, antifungal and cytotoxic effects.
A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine.
TLDR
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 and the absolute configuration of naturally occurring (+)-rubrobramid was determined by vibrational circular dichroism.
Rubrobramide, a cytotoxic and phytotoxic metabolite from Cladobotyrum rubrobrunnescens.
TLDR
Cladobotrin (1) and rubrobramide (2), possessing a unique oxidized tricyclic system, is a new compound structurally related to flavipucine (3), which also is produced by the fungus.
Talaramide A, an unusual alkaloid from the mangrove endophytic fungus Talaromyces sp. (HZ-YX1) as an inhibitor of mycobacterial PknG
An unusual alkaloid, talaramide A (1), was obtained from the mangrove endophytic fungus Talaromyces sp. (HZ-YX1). The structure of 1 was established by analysis of NMR spectroscopic data, X-ray
In vitro evaluation of the determinants of bactericidal activity of ampicillin dosing regimens against Escherichia coli
An in vitro flow model was used to examine the influence of peak concentration (Cmax), the area under the antibiotic concentration-time curve (AUC), the magnitude of AUC above the MIC, and the
The structure of isoflavipucine
The structure of isoflavipucine 2a, a remarkable rearrangement product of the antibiotic flavipucine 1, is proposed on the basis of spectral data and chemical and mechanistic considerations.
The X-ray crystal structure of (±)-flavipucine
Synthetic (±)-flavipucine (C12H15O4N) is monoclinic, space groupP21/c, with a = 11.506(5), b = 8.765(5), c = 11.981(7) A, β = 91.09(2)°, Z = 4. X-ray analysis confirms its structure as 1,
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