Synthesis of 4-azasteroids by an intramolecular Ugi reaction
In this paper we report the use of an intramolecular Ugi reaction to synthesize new 4-azacholestanes diversely substituted both at N-4 and C-5. Both the scope and the stereochemical outcome of this approach were studied by varying the nature of the components necessary for this multicomponent reacti...
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todo:paper_0039128X_v73_n12_p1270_Alonso2023-10-03T14:49:27Z Synthesis of 4-azasteroids by an intramolecular Ugi reaction Alonso, F. Acebedo, S.L. Bruttomesso, A.C. Ramírez, J.A. 4-Azacholestanes Azasterols Multicomponent reaction Ugi reaction 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one azasteroid cholestane derivative unclassified drug article chemical reaction drug synthesis drug targeting stereochemistry substitution reaction Azasteroids Magnetic Resonance Spectroscopy Molecular Conformation Spectrometry, Mass, Electrospray Ionization In this paper we report the use of an intramolecular Ugi reaction to synthesize new 4-azacholestanes diversely substituted both at N-4 and C-5. Both the scope and the stereochemical outcome of this approach were studied by varying the nature of the components necessary for this multicomponent reaction. In sight of our results we concluded that this methodology can be applied to obtain 4-azasteroids targeted to find new biologically active compounds. © 2008 Elsevier Inc. All rights reserved. Fil:Acebedo, S.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Bruttomesso, A.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v73_n12_p1270_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-Azacholestanes Azasterols Multicomponent reaction Ugi reaction 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one azasteroid cholestane derivative unclassified drug article chemical reaction drug synthesis drug targeting stereochemistry substitution reaction Azasteroids Magnetic Resonance Spectroscopy Molecular Conformation Spectrometry, Mass, Electrospray Ionization |
| spellingShingle |
4-Azacholestanes Azasterols Multicomponent reaction Ugi reaction 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one azasteroid cholestane derivative unclassified drug article chemical reaction drug synthesis drug targeting stereochemistry substitution reaction Azasteroids Magnetic Resonance Spectroscopy Molecular Conformation Spectrometry, Mass, Electrospray Ionization Alonso, F. Acebedo, S.L. Bruttomesso, A.C. Ramírez, J.A. Synthesis of 4-azasteroids by an intramolecular Ugi reaction |
| topic_facet |
4-Azacholestanes Azasterols Multicomponent reaction Ugi reaction 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' (1h benzo[b]azol 3 yl)ethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 (2' phenylethyl) 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 (3' azidopropyl) 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (diethoxyphosphorylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n (methoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 benzyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5alpha cholestan 3 one 4 butyl 5 n cyclohexylcarboxamido 4 aza 5beta cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5alpha cholestan 3 one 4 propargyl 5 n (ethoxycarbonylmethylen)carboxamido 4 aza 5beta cholestan 3 one azasteroid cholestane derivative unclassified drug article chemical reaction drug synthesis drug targeting stereochemistry substitution reaction Azasteroids Magnetic Resonance Spectroscopy Molecular Conformation Spectrometry, Mass, Electrospray Ionization |
| description |
In this paper we report the use of an intramolecular Ugi reaction to synthesize new 4-azacholestanes diversely substituted both at N-4 and C-5. Both the scope and the stereochemical outcome of this approach were studied by varying the nature of the components necessary for this multicomponent reaction. In sight of our results we concluded that this methodology can be applied to obtain 4-azasteroids targeted to find new biologically active compounds. © 2008 Elsevier Inc. All rights reserved. |
| format |
JOUR |
| author |
Alonso, F. Acebedo, S.L. Bruttomesso, A.C. Ramírez, J.A. |
| author_facet |
Alonso, F. Acebedo, S.L. Bruttomesso, A.C. Ramírez, J.A. |
| author_sort |
Alonso, F. |
| title |
Synthesis of 4-azasteroids by an intramolecular Ugi reaction |
| title_short |
Synthesis of 4-azasteroids by an intramolecular Ugi reaction |
| title_full |
Synthesis of 4-azasteroids by an intramolecular Ugi reaction |
| title_fullStr |
Synthesis of 4-azasteroids by an intramolecular Ugi reaction |
| title_full_unstemmed |
Synthesis of 4-azasteroids by an intramolecular Ugi reaction |
| title_sort |
synthesis of 4-azasteroids by an intramolecular ugi reaction |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v73_n12_p1270_Alonso |
| work_keys_str_mv |
AT alonsof synthesisof4azasteroidsbyanintramolecularugireaction AT acebedosl synthesisof4azasteroidsbyanintramolecularugireaction AT bruttomessoac synthesisof4azasteroidsbyanintramolecularugireaction AT ramirezja synthesisof4azasteroidsbyanintramolecularugireaction |
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1807322874912964608 |