title: Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Fernando
authors.initials: F
authors.lastname: Alonso
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Adriana M
authors.initials: AM
authors.lastname: Cirigliano
authors.affiliation: Departamento de Química Biológica and IQUIBICEN, (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 4, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: María Eugenia
authors.initials: ME
authors.lastname: Dávola
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Gabriela M
authors.initials: GM
authors.lastname: Cabrera
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Guadalupe E
authors.initials: GE
authors.lastname: García Liñares
authors.affiliation: Laboratorio de Glicobilogía, Fundación Instituto Leloir e Instituto de Investigaciones Bioquímicas de Buenos Aires, Avenida Patricias Argentinas 435, C1405BWE Buenos Aires, Argentina.
authors.forename: Carlos
authors.initials: C
authors.lastname: Labriola
authors.affiliation: Departamento de Química Biológica and IQUIBICEN, (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 4, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Andrea A
authors.initials: AA
authors.lastname: Barquero
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina. Electronic address: jar@qo.fcen.uba.ar.
authors.forename: Javier A
authors.initials: JA
authors.lastname: Ramírez
mesh_terms: D000818:Animals; D002522:Chlorocebus aethiops; D005057:Eukaryotic Cells / Q000187:drug effects*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013261:Sterols / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D014709:Vero Cells
chemical_list: D013261:Sterols
keywords: 4,4-Dimethyl sterols; Antifungal; Cytotoxic; Ugi reaction