Ipomoeassin F is a resin glycoside that is very cytotoxic towards many cancer cell lines with IC<sub>50</sub> values in the double-digit or even single-digit nanomolar range. From previous work, it is known that the aglycone is important. For example, ipomoeassin A and F only differ by the length of the fatty acid chain, but the cytotoxicity drops 4-13 fold in ipomoeassin A. However, further information on how modifications of the aglycone would affect biological activity is still missing. To address this knowledge gap, new ipomoeassin F analogues allowing for tail modification at the aglycone was designed. Starting from commercially available starting materials, several tail-modified analogs were synthesized to explore the function of the aglycone on the biological activity. In the future, further elaborated studies based on this preliminary work will enrich structure–activity relationship information and facilitate the process of understanding ipomoeassin F’s mode of action.

Synthesis of ipomoeassin F analogs with a tail modified aglycone

254th National Meeting (2017)

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