Abstract

Enantiomerically pure (2R,3S)-disubstituted tetrahydropyrans with diverse functional groups were synthesized. These derivatives were used as a model to study the influence of the tert-butyl dimethyl silyl group in the anticancer activity. The in vitro cytotoxicity was evaluated against a panel of six human cancer cells from diverse origin (MCF7, T-47D, HeLa, SW1573, WiDr and A2780). The structure-activity relationship study shows the relevant role of the silyl protecting group in the enhancement of the observed cytotoxic activity.

Keywords: Silyl ethers, antitumor agents, structure-activity relationships, lipophilicity, drug design