Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues

Abstract: Analogues of the anticancer natural product oximidine II were prepared and evaluated for cytotoxicity. One analogue of oximidine II that carries a C15 allylic amide side chain as well as two analogues with C15 vinyl sulfone side chains were found to lack cytotoxicity against the cancer cell line SK‐Mel‐5, thereby confirming the necessity of the C15 enamide side chain of oximidine II for cytotoxicity. Four analogues, designed by comparative molecular similarity index analysis (CoMSIA), that feature a less complex macrolactone scaffold were prepared and tested. The two analogues carrying a C15 vinyl sulfone group and the two analogues with a C15 oximidine II enamide side chain showed weak cytotoxicity against the SK‐Mel‐5 cell line and other cell lines, indicating that the designed simplified macrocycles cannot replace the oximidine II macrocycle.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues ; volume:11 ; number:15 ; year:2016 ; pages:1600-1616 ; extent:17
ChemMedChem ; 11, Heft 15 (2016), 1600-1616 (gesamt 17)

Creator
Schneider, Christopher M.
Li, Wei
Khownium, Kriangsak
Lushington, Gerald H.
Georg, Gunda I.

DOI
10.1002/cmdc.201600024
URN
urn:nbn:de:101:1-2022110706502047185258
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:21 AM CEST

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Associated

  • Schneider, Christopher M.
  • Li, Wei
  • Khownium, Kriangsak
  • Lushington, Gerald H.
  • Georg, Gunda I.

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