Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells

• Analogues of 4,4-dimethyl sterols with a diamide side chain were synthetized.
• The synthesis involved a multicomponent Ugi reaction.
• Some compounds showed a selective activity against the fungal plant pathogen Fusarium.
• A by-product of the synthesis resulted cytotoxic against mammalian cells.

Most sterols, such as cholesterol and ergosterol, become functional only after the removal of the two methyl groups at C-4 from their biosynthetic precursors. Nevertheless, some findings suggest that 4,4-dimethyl sterols might be involved in specific physiological processes. In this paper we present the synthesis of a collection of analogues of 4,4-dimethyl sterols with a diamide side chain and a preliminary analysis of their in vitro activity on selected biological systems. The key step for the synthesis involves an Ugi condensation, a versatile multicomponent reaction. Some of the new compounds showed antifungal and cytotoxic activity.

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