کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1368697 | 981706 | 2016 | 4 صفحه PDF | دانلود رایگان |
A stereoselective total synthesis of (−)-cleistenolide (1) from d-glucose has been achieved. This new approach for the synthesis of (−)-cleistenolide and analogues involves a one-C-atom degradation of the chiral precursor, (Z)-selective Wittig olefination, followed by the final δ-lactonisation. Synthesized compounds showed potent growth inhibitory effects against selected human tumour cell lines, especially 2,4,6-trichlorobenzoyl derivative 12, which in the culture of MDA-MB 231 cells displayed the highest activity (IC50 0.02 μM) of all compounds under evaluation. A preliminary SAR study reveals the structural features that are beneficial for antiproliferative activity of synthesized δ-lactones, such as presence of either electron-withdrawing or electron-donating substituents in the aromatic ring, as well as the presence of cinnamoyl functionality instead of benzoyl group at the O-7 position.
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Journal: Bioorganic & Medicinal Chemistry Letters - Volume 26, Issue 14, 15 July 2016, Pages 3318–3321