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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.

SUBMITTER: Schneider CM

PROVIDER: S-EPMC4987132 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues.

Schneider Christopher M CM Li Wei W Khownium Kriangsak K Lushington Gerald H GH Georg Gunda I GI

ChemMedChem 20160531 15

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 featu ...[more]

PMID: 27240557

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