Abstract:
3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.
Registro:
Documento: |
Artículo
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Título: | Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone |
Autor: | Eduardo, S.L.; Ghini, A.A.; Burton, G. |
Filiación: | Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
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Palabras clave: | 2,19-Oxido-allopregnanolone; 4,19-oxido-allopregnanolone; Neurosteroid; Oxido-bridged steroid; 19 hydroxy 2alpha,3alpha epoxypregnane; 19 hydroxypregnenolone 3 acetate; 3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one; 3alpha hydroxy 5alphah pregnan 20 one; 4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one; bridged compound; neurosteroid; silane derivative; unclassified drug; article; cyclization; desilylation; drug structure; drug synthesis; structure activity relation |
Año: | 2003
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Volumen: | 2003
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Número: | 10
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Página de inicio: | 468
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Página de fin: | 476
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Título revista: | Arkivoc
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Título revista abreviado: | Arkivoc
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ISSN: | 14246376
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PDF: | https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2003_n10_p468_Eduardo.pdf |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p468_Eduardo |
Referencias:
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- Burton, G., Galignana, M.D., De Lavallaz, S., Brachet-Cota, A.L., Sproviero, E.M., Ghini, A.A., Lantos, C.P., Damasco, M.C., (1995) Mol. Pharmacol., 47, p. 535
- Stone, T.W., (1996) CNS Neurotransmitters and Neuromodulators. Neuroactive Steroids, , Chapters 2 and 4, CRC Press
- Veleiro, A.S., Rosenstein, R., Jaliffa, C., Grilli, M.L., Speroni, F., Burton, G., (2003) Bioorg. Med Chem. Letters, 13, p. 343
- Anderson, A., Boyd, A.C., Clark, J.K., Fielding, L., Gemmell, D.K., Hamilton, N.M., Maidment, M.S., Taylor, R., (2000) J. Med. Chem., 43, p. 4118
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- Joselevich, M., Ghini, A.A., Burton, G., (2003) Org. Biomol. Chem., 1, p. 939
- note; note; note; Haasnoot, C.A.G., De Leew, F.A.A.M., Altona, C., (1980) Tetrahedron, 36, p. 2783
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Citas:
---------- APA ----------
Eduardo, S.L., Ghini, A.A. & Burton, G.
(2003)
. Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone. Arkivoc, 2003(10), 468-476.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p468_Eduardo [ ]
---------- CHICAGO ----------
Eduardo, S.L., Ghini, A.A., Burton, G.
"Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone"
. Arkivoc 2003, no. 10
(2003) : 468-476.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p468_Eduardo [ ]
---------- MLA ----------
Eduardo, S.L., Ghini, A.A., Burton, G.
"Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone"
. Arkivoc, vol. 2003, no. 10, 2003, pp. 468-476.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p468_Eduardo [ ]
---------- VANCOUVER ----------
Eduardo, S.L., Ghini, A.A., Burton, G. Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone. Arkivoc. 2003;2003(10):468-476.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p468_Eduardo [ ]