Novel (−)-goniofufurone mimics: Synthesis, antiproliferative activity and SAR analysis

Divergent syntheses of novel (?)-goniofufurone mimics with an alkoxymethyl group as the side chain have been accomplished from D-glucose in nine synthetic steps and in overall yields 6.7?8.7 %. Their in vitro antiproliferative activity was evaluated against eight human tumour cell lines as well as a...

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Published inJournal of the Serbian Chemical Society Vol. 84; no. 12; pp. 1345 - 1353
Main Authors Sreco-Zelenovic, Bojana, Kekezovic, Sladjana, Popsavin, Mirjana, Kojic, Vesna, Benedekovic, Goran, Popsavin, Velimir
Format Journal Article
LanguageEnglish
Published Serbian Chemical Society 2019
Subjects
antitumour agents
cytotoxic lactones
d-glucose
goniofufurone mimics
structure-activity relationships
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Summary:Divergent syntheses of novel (?)-goniofufurone mimics with an alkoxymethyl group as the side chain have been accomplished from D-glucose in nine synthetic steps and in overall yields 6.7?8.7 %. Their in vitro antiproliferative activity was evaluated against eight human tumour cell lines as well as a single normal cell line. All analogues demonstrated powerful to good antiproliferative effects toward all malignant cell lines under evaluation. Against the HL-60 cell line, all mimics showed increased activities being 27- to 1604-fold more potent than the lead compound, (?)-goniofufurone. Remarkably, the majority of synthesized analogues displayed higher or similar activity to the commercial antitumour agent doxorubicin (DOX) against A549 cell line. The most potent compound exhibited 196-fold stronger cytotoxicity than DOX in the culture of this cell line. nema
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC190912104S