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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todo:paper_0039128X_v84_n_p1_Alonso2023-10-03T14:49:33Z Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells Alonso, F. Cirigliano, A.M. Dávola, M.E. Cabrera, G.M. García Liñares, G.E. Labriola, C. Barquero, A.A. Ramírez, J.A. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p1_Alonso |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 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 |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Alonso, F. Cirigliano, A.M. Dávola, M.E. Cabrera, G.M. García Liñares, G.E. Labriola, C. Barquero, A.A. Ramírez, J.A. |
| author_facet |
Alonso, F. Cirigliano, A.M. Dávola, M.E. Cabrera, G.M. García Liñares, G.E. Labriola, C. Barquero, A.A. Ramírez, J.A. |
| author_sort |
Alonso, F. |
| title |
Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| title_short |
Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| title_full |
Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| title_fullStr |
Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| title_full_unstemmed |
Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| title_sort |
multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p1_Alonso |
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