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

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Detalles Bibliográficos
Autores principales: Alonso, F., Cirigliano, A.M., Dávola, M.E., Cabrera, G.M., García Liñares, G.E., Labriola, C., Barquero, A.A., Ramírez, J.A.
Formato: JOUR
Materias:
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
human
nuclear magnetic resonance spectroscopy
Vero cell line
Animals
Cercopithecus aethiops
Eukaryotic Cells
Humans
Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization
Sterols
Vero Cells
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p1_Alonso
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

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