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

ALONSO F, CIRIGLIANO AM, DÁVOLA ME, CABRERA GM, GARCÍA LIÑARES GE, LABRIOLA C, BARQUERO A, RAMÍREZ JA

STEROIDS

ELSEVIER SCIENCE INC

Lugar: San Francisco; Año: 2014 vol. 84 p. 1 - 6

0039-128X

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.