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https://open.uns.ac.rs/handle/123456789/28389
Title: | Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies | Authors: | Popsavin Velimir Francuz Jovana Srećo Zelenović Bojana Benedeković Goran Popsavin Mirjana Kojić Vesna Bogdanović Gordana |
Issue Date: | 2013 | Journal: | Bioorganic and Medicinal Chemistry Letters | Abstract: | Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. © 2013 Elsevier Ltd. All rights reserved. | URI: | https://open.uns.ac.rs/handle/123456789/28389 | ISSN: | 0960-894X | DOI: | 10.1016/j.bmcl.2013.08.069 |
Appears in Collections: | PMF Publikacije/Publications |
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