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.
Original language | English (US) |
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Pages (from-to) | 1600-1616 |
Number of pages | 17 |
Journal | ChemMedChem |
DOIs | |
State | Published - 2016 |
Bibliographical note
Publisher Copyright:© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Keywords
- antitumor agents
- benzolactone enamides
- cytotoxicity
- natural products
- oximidines