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https://open.uns.ac.rs/handle/123456789/30211
Title: | Design, synthesis and SAR analysis of antitumour styryl lactones related to (+)-crassalactones B and C | Authors: | Benedeković, Goran Popsavin, Mirjana Francuz, Jovana Kovačević, Ivana Kojić, Vesna Bogdanović Gordana Divjaković Vladimir Popsavin, Velimir |
Issue Date: | 2014 | Journal: | European Journal of Medicinal Chemistry | Abstract: | © 2014 Elsevier Masson SAS. A series of styryl lactones containing the cinnamic acid ester groups such as (+)-crassalactones B (3a) and C (4a), 5,7-di-O-cinamoyl derivative 6, the corresponding 7-epimers and 7-deoxy derivatives have been synthesized, characterized and evaluated for their in vitro antitumour activity against a panel of several human tumour cell lines. Twelve new analogues such as 5-O-or 7-O-(4-methoxycinnamoyl), 5-O-or 7-O-(4-nitrocinnamoyl) and 5-O-or 7-O-(4-fluorocinnamoyl) esters of (+)-goniofufurone (3b-d), 7-epi-(+)-goniofufurone (epi-3b-d), as well as 7-deoxy derivatives 5b-d have been prepared to correlate all compounds in a SAR study. Some of the analogues displayed powerful antiproliferative effects on selected human tumour cell lines, but none of them demonstrated cytotoxicity towards the normal foetal lung fibroblasts (MRC-5). Thus, for the 7-epi-crassalactone B (epi-3a) was found to be a potent inhibitor of HL-60 cells growth, with an IC50value that is approximately 46-fold lower than that observed for the commercial antitumour drug doxorubicin in the culture of the same cells. A SAR analysis performed on these lactones reveals the main structural features that affect their antiproliferative activity, such as nature of the substituents at the C-4 in the aromatic rings of cinnamoyl moieties, the absolute stereochemistry, as well as the presence of a deoxy function at the C-7 position. | URI: | https://open.uns.ac.rs/handle/123456789/30211 | ISSN: | 0223-5234 | DOI: | 10.1016/j.ejmech.2014.09.064 (BISIS)90674 |
Appears in Collections: | MDF Publikacije/Publications |
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