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Issue 2, 2017
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Natural diarylfluorene derivatives: isolation, total synthesis, and phosphodiesterase-4 inhibition

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Abstract

In our previous study, selaginpulvilins A–D (1–4) featuring an unprecedented 9,9-diphenyl-1-(phenylethynyl)-9H-fluorene skeleton were identified as potent phosphodiesterase-4 (PDE4) inhibitors from Selaginella pulvinata. In the current work, a large-scale reinvestigation of the same plant led to the isolation of six additional new analogues, selaginpulvilins E–J (5–10), among which 5 features a rare 6-(4-hydroxyphenyl)-2H-pyran-2-one unit. Compounds 5–10 exhibited remarkable inhibitory activities against PDE4 with IC50 values in the range of 0.22–1.38 μM. The first total synthesis of selaginpulvilins A–F (1–6) was developed in 7–11 steps involving a Friedel–Crafts reaction as the key reaction, which provides a feasible access to this scaffold.

Graphical abstract: Natural diarylfluorene derivatives: isolation, total synthesis, and phosphodiesterase-4 inhibition

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Supplementary files

Article information


Submitted
12 Oct 2016
Accepted
15 Nov 2016
First published
23 Nov 2016

Org. Chem. Front., 2017,4, 170-177
Article type
Research Article

Natural diarylfluorene derivatives: isolation, total synthesis, and phosphodiesterase-4 inhibition

J. Zhang, X. Liu, J. Weng, Y. Guo, Q. Li, A. Ahmed, G. Tang and S. Yin, Org. Chem. Front., 2017, 4, 170
DOI: 10.1039/C6QO00623J

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