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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2008
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v73_n12_p1270_Alonso http://hdl.handle.net/20.500.12110/paper_0039128X_v73_n12_p1270_Alonso |
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paper:paper_0039128X_v73_n12_p1270_Alonso2023-06-08T15:03:18Z Synthesis of 4-azasteroids by an intramolecular Ugi reaction Acebedo, Sofìa Lorena Bruttomesso, Andrea Claudia Ramirez, Javier Alberto 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. 2008 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v73_n12_p1270_Alonso http://hdl.handle.net/20.500.12110/paper_0039128X_v73_n12_p1270_Alonso |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
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 Acebedo, Sofìa Lorena Bruttomesso, Andrea Claudia Ramirez, Javier Alberto 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. |
| author |
Acebedo, Sofìa Lorena Bruttomesso, Andrea Claudia Ramirez, Javier Alberto |
| author_facet |
Acebedo, Sofìa Lorena Bruttomesso, Andrea Claudia Ramirez, Javier Alberto |
| author_sort |
Acebedo, Sofìa Lorena |
| 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 |
| publishDate |
2008 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v73_n12_p1270_Alonso http://hdl.handle.net/20.500.12110/paper_0039128X_v73_n12_p1270_Alonso |
| work_keys_str_mv |
AT acebedosofialorena synthesisof4azasteroidsbyanintramolecularugireaction AT bruttomessoandreaclaudia synthesisof4azasteroidsbyanintramolecularugireaction AT ramirezjavieralberto synthesisof4azasteroidsbyanintramolecularugireaction |
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1768546151720550400 |