Natural diarylfluorene derivatives: isolation, total synthesis, and phosphodiesterase-4 inhibition. Issue 2 (30th November 2016)

• Record Type: Journal Article
• Authors: Zhang, Jun-Sheng; Liu, Xin; Weng, Jiang; Guo, Yan-Qiong; Li, Qing-Jiang; Ahmed, Abrar; Tang, Gui-Hua; Yin, Sheng
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 2(2017)
• Page Start: 170
• Page End: 177
• Publication Date: 2016-11-30
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00623j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The first total synthesis of selaginpulvilins A–F and evaluation of their PDE4 inhibitory activities. Abstract : In our previous study, selaginpulvilins A–D (1–4 ) featuring an unprecedented 9, 9-diphenyl-1-(phenylethynyl)-9 H -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 which5 features a rare 6-(4-hydroxyphenyl)-2 H -pyran-2-one unit. Compounds5–10 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.