Please use this identifier to cite or link to this item:
https://open.uns.ac.rs/handle/123456789/20604
DC Field | Value | Language |
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dc.contributor.author | Benedeković Goran | - |
dc.contributor.author | Popsavin Mirjana | - |
dc.contributor.author | Kovačević Ivana | - |
dc.contributor.author | Kojić Vesna | - |
dc.contributor.author | Rodić Marko | - |
dc.contributor.author | Popsavin Velimir | - |
dc.date.accessioned | 2020-12-13T14:53:45Z | - |
dc.date.available | 2020-12-13T14:53:45Z | - |
dc.date.issued | 2020 | - |
dc.identifier.issn | 0223-5234 | - |
dc.identifier.uri | https://open.uns.ac.rs/handle/123456789/20604 | - |
dc.description.abstract | © 2020 Elsevier Masson SAS A new, modified total synthesis of (−)-cleistenolide (1) and sixteen new analogues or derivatives was achieved starting from commercially available 1,2-O-isopropylidene-α-D-glucofuranose. The synthesis of 1 proceeds in six steps and 67% overall yield, using single-carbon atom degradation of a protected chiral precursor, (Z)-selective Wittig olefination, and acid catalyzed δ-lactonization. A new Lewis acid promoted procedure for one-pot O-debenzylation/O-acylation has been developed to complete the synthesis of natural product 1 and selected analogues. The synthesized compounds were tested in vitro to evaluate their cytotoxicity against K562, HL-60, Jurkat, Raji, MCF-7, MDA-MB 231, HeLa, A549, and MRC-5 cell lines. All (−)-cleistenolide analogues exhibited significantly higher cytotoxicity than lead 1 against the majority of cell lines tested. Most of the synthesized compounds are more active than doxorubicin on at least one malignant cell line, but were almost completely inactive against normal MRC-5 cells. The structural features of the tested compounds responsible for their antiproliferative activity have been identified by preliminary SAR analysis. | en |
dc.language.iso | en | - |
dc.relation.ispartof | European Journal of Medicinal Chemistry | en |
dc.source | CRIS UNS | - |
dc.source.uri | http://cris.uns.ac.rs | - |
dc.title | Synthesis, antiproliferative activity and SAR analysis of (−)-cleistenolide and analogues | en |
dc.type | Journal/Magazine Article | en |
dc.identifier.doi | 10.1016/j.ejmech.2020.112597 | - |
dc.identifier.scopus | 85087746009 | - |
dc.identifier.url | https://www.cris.uns.ac.rs/record.jsf?recordId=115844&source=BEOPEN&language=en | en |
dc.relation.volume | 202 | - |
dc.identifier.externalcrisreference | (BISIS)115844 | - |
item.fulltext | No Fulltext | - |
item.grantfulltext | none | - |
crisitem.author.dept | Prirodno-matematički fakultet, Departman za hemiju, biohemiju i zaštitu životne sredine | - |
crisitem.author.dept | Prirodno-matematički fakultet, Departman za hemiju, biohemiju i zaštitu životne sredine | - |
crisitem.author.dept | Prirodno-matematički fakultet, Departman za hemiju, biohemiju i zaštitu životne sredine | - |
crisitem.author.dept | Medicinski fakultet | - |
crisitem.author.dept | Prirodno-matematički fakultet, Departman za hemiju, biohemiju i zaštitu životne sredine | - |
crisitem.author.dept | Prirodno-matematički fakultet, Departman za hemiju, biohemiju i zaštitu životne sredine | - |
crisitem.author.orcid | 0000-0002-4752-7569 | - |
crisitem.author.orcid | 0000-0002-0924-1041 | - |
crisitem.author.orcid | 0000-0002-4471-8001 | - |
crisitem.author.orcid | 0000-0001-9910-2987 | - |
crisitem.author.parentorg | Prirodno-matematički fakultet | - |
crisitem.author.parentorg | Prirodno-matematički fakultet | - |
crisitem.author.parentorg | Prirodno-matematički fakultet | - |
crisitem.author.parentorg | Univerzitet u Novom Sadu | - |
crisitem.author.parentorg | Prirodno-matematički fakultet | - |
crisitem.author.parentorg | Prirodno-matematički fakultet | - |
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