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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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Publication details

The article was received on 12 Oct 2016, accepted on 15 Nov 2016 and first published on 23 Nov 2016


Article type: Research Article
DOI: 10.1039/C6QO00623J
Citation: Org. Chem. Front., 2017,4, 170-177
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    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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