Please use this identifier to cite or link to this item:
https://open.uns.ac.rs/handle/123456789/18704
Title: | Conformationally restricted goniofufurone mimics with halogen, azido or benzoyloxy groups at the C-7 position: Design, synthesis and antiproliferative activity | Authors: | Svirčev Miloš Benedeković Goran Kovačević Ivana Popsavin Mirjana Kojić Vesna Jakimov Dimitar Srdić Rajić Tatjana Rodić Marko Popsavin Velimir |
Issue Date: | 2018 | Journal: | Tetrahedron | Abstract: | © 2018 Elsevier Ltd A series of new conformationally restricted goniofufurone mimics, bearing an additional 1,3-dioxan ring and a halogen, azido or benzoyloxy functionality at the C-7 position has been designed and synthesized. The Appel reaction was used for replacement of 7-OH group with Cl or Br functions in tricyclic lactone (3). 7-Iodo derivative (3d) was prepared by using the Ph3P/I2/2,6-lutidine reagent system. 7-Fluoro group was introduced by treatment of 3 with DAST, while the corresponding 7-azido and 7-benzoyloxy derivatives have been prepared by multistep sequences. Synthesized products were evaluated for their ability to inhibit growth of selected human malignant cell lines. Structure-activity relationships demonstrated that the nature of a substituent at the C-7 position could enhance the antiproliferative activity of the analogues. The preliminary study on the mechanisms indicated that all synthesized compounds induced apoptosis in 61–77% of K562 cells. | URI: | https://open.uns.ac.rs/handle/123456789/18704 | ISSN: | 0040-4020 | DOI: | 10.1016/j.tet.2018.07.046 |
Appears in Collections: | PMF Publikacije/Publications |
Show full item record
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.