Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR
A new methodology to obtain C-25 and C-26 steroidal acids starting from pregnenolone is described. Construction of the side chain was achieved by applying the Mukaiyama aldol reaction with a non-hydrolytic work-up to isolate the trapped silyl enol ether with higher yields. Using this methodology we...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0039128X_v121_n_p40_Dansey |
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todo:paper_0039128X_v121_n_p40_Dansey2023-10-03T14:49:19Z Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR Dansey, M.V. del Fueyo, M.C. Veleiro, A.S. Di Chenna, P.H. Dafachronic acids Glucocorticoids Mukaiyama reaction Oxysterols Steroidal acids cell nucleus receptor cholestane derivative ether derivative glucocorticoid receptor ligand liver X receptor nuclear receptor DAF 12 pregnenolone silane derivative steroid unclassified drug cell receptor dafachronic acid glucocorticoid receptor liver X receptor steroid Article biological activity chemical modification drug receptor binding drug synthesis Mukaiyama reaction quantum yield reporter gene chemical structure chemistry hydrolysis metabolism nuclear magnetic resonance spectroscopy synthesis Cholestenes Hydrolysis Liver X Receptors Magnetic Resonance Spectroscopy Molecular Structure Receptors, Cytoplasmic and Nuclear Receptors, Glucocorticoid Steroids A new methodology to obtain C-25 and C-26 steroidal acids starting from pregnenolone is described. Construction of the side chain was achieved by applying the Mukaiyama aldol reaction with a non-hydrolytic work-up to isolate the trapped silyl enol ether with higher yields. Using this methodology we synthesized three new steroidal acids as potential ligands of DAF-12, Liver X and Glucocorticoid nuclear receptors and studied their activity in reporter gene assays. Our results show that replacement of the 21-CH3 by a 20-keto group in the side chains of the cholestane scaffold of DAF-12 or Liver X receptors ligands causes the loss of the activity. © 2017 Elsevier Inc. Fil:Dansey, M.V. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Veleiro, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Di Chenna, P.H. 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_v121_n_p40_Dansey |
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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 |
Dafachronic acids Glucocorticoids Mukaiyama reaction Oxysterols Steroidal acids cell nucleus receptor cholestane derivative ether derivative glucocorticoid receptor ligand liver X receptor nuclear receptor DAF 12 pregnenolone silane derivative steroid unclassified drug cell receptor dafachronic acid glucocorticoid receptor liver X receptor steroid Article biological activity chemical modification drug receptor binding drug synthesis Mukaiyama reaction quantum yield reporter gene chemical structure chemistry hydrolysis metabolism nuclear magnetic resonance spectroscopy synthesis Cholestenes Hydrolysis Liver X Receptors Magnetic Resonance Spectroscopy Molecular Structure Receptors, Cytoplasmic and Nuclear Receptors, Glucocorticoid Steroids |
| spellingShingle |
Dafachronic acids Glucocorticoids Mukaiyama reaction Oxysterols Steroidal acids cell nucleus receptor cholestane derivative ether derivative glucocorticoid receptor ligand liver X receptor nuclear receptor DAF 12 pregnenolone silane derivative steroid unclassified drug cell receptor dafachronic acid glucocorticoid receptor liver X receptor steroid Article biological activity chemical modification drug receptor binding drug synthesis Mukaiyama reaction quantum yield reporter gene chemical structure chemistry hydrolysis metabolism nuclear magnetic resonance spectroscopy synthesis Cholestenes Hydrolysis Liver X Receptors Magnetic Resonance Spectroscopy Molecular Structure Receptors, Cytoplasmic and Nuclear Receptors, Glucocorticoid Steroids Dansey, M.V. del Fueyo, M.C. Veleiro, A.S. Di Chenna, P.H. Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR |
| topic_facet |
Dafachronic acids Glucocorticoids Mukaiyama reaction Oxysterols Steroidal acids cell nucleus receptor cholestane derivative ether derivative glucocorticoid receptor ligand liver X receptor nuclear receptor DAF 12 pregnenolone silane derivative steroid unclassified drug cell receptor dafachronic acid glucocorticoid receptor liver X receptor steroid Article biological activity chemical modification drug receptor binding drug synthesis Mukaiyama reaction quantum yield reporter gene chemical structure chemistry hydrolysis metabolism nuclear magnetic resonance spectroscopy synthesis Cholestenes Hydrolysis Liver X Receptors Magnetic Resonance Spectroscopy Molecular Structure Receptors, Cytoplasmic and Nuclear Receptors, Glucocorticoid Steroids |
| description |
A new methodology to obtain C-25 and C-26 steroidal acids starting from pregnenolone is described. Construction of the side chain was achieved by applying the Mukaiyama aldol reaction with a non-hydrolytic work-up to isolate the trapped silyl enol ether with higher yields. Using this methodology we synthesized three new steroidal acids as potential ligands of DAF-12, Liver X and Glucocorticoid nuclear receptors and studied their activity in reporter gene assays. Our results show that replacement of the 21-CH3 by a 20-keto group in the side chains of the cholestane scaffold of DAF-12 or Liver X receptors ligands causes the loss of the activity. © 2017 Elsevier Inc. |
| format |
JOUR |
| author |
Dansey, M.V. del Fueyo, M.C. Veleiro, A.S. Di Chenna, P.H. |
| author_facet |
Dansey, M.V. del Fueyo, M.C. Veleiro, A.S. Di Chenna, P.H. |
| author_sort |
Dansey, M.V. |
| title |
Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR |
| title_short |
Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR |
| title_full |
Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR |
| title_fullStr |
Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR |
| title_full_unstemmed |
Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR |
| title_sort |
synthesis of new c-25 and c-26 steroidal acids as potential ligands of the nuclear receptors daf-12, lxr and gr |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v121_n_p40_Dansey |
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