کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1399193 1501153 2013 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates and their action towards cancer cells
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates and their action towards cancer cells
چکیده انگلیسی

Synthesis of the naturally occurred C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates was carried out by decarbonylative Heck reaction and selenium dioxide catalysed oxidation, respectively. In the decarbonylative Heck synthetic route, fusion of benzoyl chloride and styrene derivatives was catalysed by an N-heterocyclic carbene system generated in situ by palladium acetate and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride to form a E-tetrahydroxystilbene derivative. Formation of allyl ether was subsequently carried out by reaction of the deprotected OH in the A phenyl ring of the stilbene with 3,3-dimethylallyl bromide and a base (sodium hydride) to form O-prenylated tetrahydroxystilbene derivatives. [1,5]-Rearrangement of the isoprenyl unit from O- to C-position in the A ring was carried out at elevated temperature in the presence of magnesium silicate (Florisil) to form the corresponding C-prenylated tetrahydroxystilbene. Formation of O-prenylated cinnamate was first carried out by base catalysed allyl ether formation between 3,3-dimethylallyl bromide and hydroxycinnamic acid methyl ester. The methyl group of the isoprenyl unit was subsequently oxidized using selenium dioxide to form a terminal hydroxyl group. The prenylated tetrahydroxystilbenes and cinnamate synthesized in this study were novel derivatives of piceatannol and methyl 4-(3′-methylbut-2′-enyloxy)cinnamate isolated from propolis in Kangaroo Island, South Australia. The synthetic compounds were tested against K562 cancer cells and potent growth inhibitory activity was observed for E-1-[5-hydroxy-3-methoxy-2-(3-methyl-2-butenyl)phenyl]-2-[4-hydroxy-3-methoxyphenyl]ethene, IC50 = 0.10 μM.

A series of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates have been synthesized and evaluated for their anticancer activity.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of novel compounds recently isolated from Kangaroo Island propolis.
► Synthesis of novel prenylated tetrahydroxystilbenes and O-prenylated cinnamates.
► [1,5]-Rearrangement of 3-O-prenyl- to 2-C-prenyl-piceatannol derivatives.
► Final products were tested for activity towards K562 leukemic cancer cells.
► 2-C-prenyl-3,3′-di-O-methyl-piceatannol showed potent anticancer activity.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 63, May 2013, Pages 415–422
نویسندگان
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