Please use this identifier to cite or link to this item: https://open.uns.ac.rs/handle/123456789/26843
Title: Synthesis and biological activity of new thiazole isosteres of goniofufurone and 7-epi-goniofufurone
Authors: Svircev Milos 
Popsavin Mirjana 
Kojic Vesna 
Bogdanovic Gordana
Jadranin Milka
Popsavin Velimir 
Keywords: (+)-goniofufurone, D-glucose, thiazole, isostere, cytotoxicity
Issue Date: 2010
Journal: The 18th International Conference on Organic Synthesis, The18th International Conference on Organic Synthesis, Bergen, Norveska, 2010
Abstract: (+)-Goniofufurone is the naturally occurring cytotoxic styryl lactone isolated from the stem bark of Goniothalamus giganteus (Annonaceae) that possesses structure marked by furano-furone bicyclic core. Herein we report a total synthesis of two novel (7-epi-)goniofufurone isosteres bearing a 2-thiazolyl-4-carboxylic acid ethyl ester moiety instead of the aromatic ring at C-7. The key intermediate (4) was obtained by addition of trimethylsilyl cyanide to known aldehyde 3, which was readily available from D-glucose through a modified literature procedure. Thiazole ring was introduced in two consecutive steps (e, f), which included cyclization and oxidation, respectively, while the γ-lactone function was built in the penultimate step (h), after the deprotection of hydroxyl groups at positions C-1 and C-2 (g). After removal of benzyl protection (i), final products 1 and 2 were obtained. Antiproliferative activity of both analogues against a number of tumor cell lines will be presented.
URI: https://open.uns.ac.rs/handle/123456789/26843
Appears in Collections:PMF Publikacije/Publications

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