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Alonso, F.; Cirigliano, A.M.; Dávola, M.E.; Cabrera, G.M.; García Liñares, G.E.; Labriola, C.; Barquero, A.A.; Ramírez, J.A. "Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells" (2014) Steroids. 84:1-6
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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. © 2014 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells
Autor:Alonso, F.; Cirigliano, A.M.; Dávola, M.E.; Cabrera, G.M.; García Liñares, G.E.; Labriola, C.; Barquero, A.A.; Ramírez, J.A.
Filiación:Departamento de Química Orgánica and UMYMFOR, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 3, C1428EGA Buenos Aires, Argentina
Departamento de Química Biológica and IQUIBICEN, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 4, C1428EGA Buenos Aires, Argentina
Laboratorio de Glicobilogía, Fundación Instituto Leloir e Instituto de Investigaciones Bioquímicas de Buenos Aires, Avenida Patricias Argentinas 435, C1405BWE Buenos Aires, Argentina
Palabras clave:4,4-Dimethyl sterols; Antifungal; Cytotoxic; Keywords; Ugi reaction; (17beta) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxylate; (17beta) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxylic acid; (17beta) n ((t butylcarbamoyl)methyl) n (2 chlorophenyl) 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (2 ethyl 6 methylphenyl) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (2 fluorophenyl) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (2 naphthyl) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 chlorophenyl) 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 chlorophenyl) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 fluorophenyl) 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 fluorophenyl) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 methoxyphenyl) 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 methoxyphenyl) 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n (4 methylphenyl) 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n phenyl 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxamide; (17beta) n ((t butylcarbamoyl)methyl) n phenyl 4,4 dimethyl 3 oxoandrost 5 ene 17 carboxamide; 2 (t butylamino) 2 oxoethyl (17beta) 4,4 dimethyl 3 hydroxyandrost 5 ene 17 carboxylate; antifungal agent; sterol derivative; unclassified drug; sterol; antifungal activity; article; broth dilution; drug cytotoxicity; drug synthesis; eukaryotic cell; Fusarium; minimum inhibitory concentration; nonhuman; structure activity relation; Trypanosoma cruzi; animal; biosynthesis; chemistry; Chlorocebus aethiops; drug effects; electrospray mass spectrometry; eukaryotic cell; human; nuclear magnetic resonance spectroscopy; Vero cell line; Animals; Cercopithecus aethiops; Eukaryotic Cells; Humans; Magnetic Resonance Spectroscopy; Spectrometry, Mass, Electrospray Ionization; Sterols; Vero Cells
Año:2014
Volumen:84
Página de inicio:1
Página de fin:6
DOI: http://dx.doi.org/10.1016/j.steroids.2014.03.002
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:Sterols
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v84_n_p1_Alonso

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Citas:

---------- APA ----------
Alonso, F., Cirigliano, A.M., Dávola, M.E., Cabrera, G.M., García Liñares, G.E., Labriola, C., Barquero, A.A.,..., Ramírez, J.A. (2014) . Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells. Steroids, 84, 1-6.
http://dx.doi.org/10.1016/j.steroids.2014.03.002
---------- CHICAGO ----------
Alonso, F., Cirigliano, A.M., Dávola, M.E., Cabrera, G.M., García Liñares, G.E., Labriola, C., et al. "Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells" . Steroids 84 (2014) : 1-6.
http://dx.doi.org/10.1016/j.steroids.2014.03.002
---------- MLA ----------
Alonso, F., Cirigliano, A.M., Dávola, M.E., Cabrera, G.M., García Liñares, G.E., Labriola, C., et al. "Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells" . Steroids, vol. 84, 2014, pp. 1-6.
http://dx.doi.org/10.1016/j.steroids.2014.03.002
---------- VANCOUVER ----------
Alonso, F., Cirigliano, A.M., Dávola, M.E., Cabrera, G.M., García Liñares, G.E., Labriola, C., et al. Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells. Steroids. 2014;84:1-6.
http://dx.doi.org/10.1016/j.steroids.2014.03.002