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

FERNANDO ALONSO; ADRIANA M CIRIGLIANO; MARÍA E DÁVOLA; GABRIELA M CABRERA; GUADALUPE E GARCÍA LIÑARES; CARLOS LABRIOLA; ANDREA A BARQUERO; JAVIER ALBERTO RAMÍREZ

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.