Please use this identifier to cite or link to this item: https://open.uns.ac.rs/handle/123456789/32383
Title: Synthesis and antiproliferative activity of goniobutenolides A and B, 5-halogenated crassalactone D derivatives and the corresponding 7-epimers
Authors: Kovačević Ivana 
Popsavin Mirjana 
Benedeković Goran 
Kojić Vesna 
Jakimov Dimitar
Rodić Marko 
Srdić Rajić Tatjana
Bogdanović Gordana
Divjaković Vladimir
Popsavin Velimir 
Issue Date: 2016
Journal: European Journal of Medicinal Chemistry
Abstract: © 2015 Elsevier Masson SAS. A new synthesis of goniobutenolides A (1) and B (2) and the corresponding 7-epimers has been achieved starting from diacetone d-glucose. The key step of the synthesis is a new one-pot sequence that commenced with Z-selective Wittig (or Horner-Wadsworth-Emmons) olefination, followed by successive γ-lactonisation and β-elimination. The above-mentioned unsaturated lactones were then converted to the corresponding 5-halogenated crassalactone D derivatives by using the appropriate haloetherification protocol. The most of synthesized compounds exhibited potent cytotoxic activities against a panel of tumour cell lines. The main structural features responsible for their antitumour potency have been revealed by means of SAR analysis. Flow cytometry data suggested that cytotoxic effects of these compounds in the culture of K562 cells might be mediated by apoptosis, additionally revealing that these molecules induced changes in cell cycle distribution of these cells. Results of semi-quantitative Western blot analysis indicate that the most of synthesized compounds induce apoptosis in a caspase-dependent manner.
URI: https://open.uns.ac.rs/handle/123456789/32383
ISSN: 0223-5234
DOI: 10.1016/j.ejmech.2015.12.011
Appears in Collections:PMF Publikacije/Publications

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