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

Bojana Srećo Zelenović; Sladjana Kekezović; Mirjana Popsavin; Vesna Kojić; Goran Benedeković; Velimir Popsavin

doi:10.2298/JSC190912104S

PDF (318 kB) Supplementary Material (1.09 MB)

Published: Jan 10, 2020

DOI: https://doi.org/10.2298/JSC190912104S

Keywords:

D-glucose antitumour agents goniofufurone mimics cytotoxic lactones structure–activity relationships

Bojana Srećo Zelenović

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad

Sladjana Kekezović

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad

Mirjana Popsavin

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad

https://orcid.org/0000-0002-0924-1041

Vesna Kojić

Oncology Institute of Vojvodina, Put dr Goldmana 4, 21204 Sremska Kamenica

Goran Benedeković

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad

Velimir Popsavin

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad Serbian Academy of Sciences and Arts, Knez Mihajlova 35, 11000 Belgrade

http://orcid.org/0000-0001-9910-2987

Abstract

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.

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[1]

B. Srećo Zelenović, S. Kekezović, M. Popsavin, V. Kojić, G. Benedeković, and V. Popsavin, “Novel (−)-goniofufurone mimics: Synthesis, antiproliferative activity and SAR analysis”, J. Serb. Chem. Soc., vol. 84, no. 12, pp. 1345–1353, Jan. 2020.

Issue

Vol. 84 No. 12 (2019)

Section

Organic Chemistry

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

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