Abstract:
3α-Hydroxy-6,19-oxidopregn-4-ene-20-one (4) was prepared in seven steps from pregnanolone acetate. At 0.1 μM concentration 4 significantly increased GABA induced 36Cl- influx in hamster cerebral cortex synaptoneurosomes while at 20 mg/kg it decreased the percentage of hamsters showing seizures induced by 3-mercaptopropionic acid. © 2002 Elsevier Science Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Synthesis and GABAA receptor activity of a 6,19-oxido analogue of pregnanolone |
Autor: | Veleiro, A.S.; Rosenstein, R.E.; Jaliffa, C.O.; Grilli, M.L.; Speroni, F.; Burton, G. |
Filiación: | Depto. de Quím. Orgán., Universidad de Buenos Aires, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina
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Palabras clave: | 3 mercaptopropionic acid; 3alpha hydroxy 6,19 oxidopregn 4 en 20 one; 4 aminobutyric acid A receptor; acetic acid derivative; anticonvulsive agent; chloride ion; eltanolone; unclassified drug; animal cell; animal experiment; article; brain cortex; brain synaptosome; chloride transport; concentration response; controlled study; dose response; drug activity; drug synthesis; hamster; nonhuman; seizure; 3-Mercaptopropionic Acid; Animals; Cerebral Cortex; Convulsants; Cricetinae; Indicators and Reagents; Pregnanolone; Receptors, GABA-A; Seizures; Stereoisomerism; Structure-Activity Relationship; Synaptosomes; Cricetinae |
Año: | 2003
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Volumen: | 13
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Número: | 3
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Página de inicio: | 343
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Página de fin: | 346
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DOI: |
http://dx.doi.org/10.1016/S0960-894X(02)01019-3 |
Título revista: | Bioorganic and Medicinal Chemistry Letters
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Título revista abreviado: | Bioorg. Med. Chem. Lett.
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ISSN: | 0960894X
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CODEN: | BMCLE
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CAS: | 3 mercaptopropionic acid, 107-96-0; eltanolone, 128-20-1; 3 alpha-hydroxy-6,19-oxidopregn-4-ene-20-one; 3-Mercaptopropionic Acid, 107-96-0; Convulsants; Indicators and Reagents; Pregnanolone, 128-20-1; Receptors, GABA-A
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0960894X_v13_n3_p343_Veleiro |
Referencias:
- Sieghart, W., (1995) Pharmacol. Rev., 47, p. 182
- Baulieu, E.E., (1998) Psychoneuroendocrinol., 23, p. 963
- Baulieu, E.E., (1997) Recent Prog. Horm. Res., 52, p. 1
- Compagnone, N.A., Mellon, S.H., (2000) Front. Neuroendocrinol., 21, p. 1
- Tsutsui, K., Ukena, K., Usui, M., Sakamoto, H., Takase, M., (2000) Neurosci. Res., 36, p. 261
- Gasior, M., Carter, R.B., Witkin, J.M., (1999) Trends Pharmacol. Sci., 20, p. 107
- Lambert, J.J., Belelli, D., Hill-Venning, C., Peters, J.A., (1995) Trends Pharmacol. Sci., 16, p. 295
- Belelli, D., Lan, N.C., Gee, K.W., (1990) Neurosci. Biobehav. Rev., 14, p. 315
- Golombek, D.A., Fernández, D.D., De Brito Sánchez, M.G., Burin, L., Cardinali, D.P., (1991) Eur. J. Pharmacol., 210, p. 253
- Rogawski, M.A., Reddy, D.S., (2002) Int. Rev. Neurobiol., 49, p. 199
- Beekman, M., Ungard, J.T., Gasior, M., Carter, R.B., Dijkstra, D., Golberg, S.R., Witkin, J.M., (1998) J. Pharmacol. Exp. Ther., 284, p. 868
- Upasani, R.B., Yang, K.C., Acosta-Burruel, M., Konkoy, C.S., McLellan, J.A., Woodward, R.M., Lan, N.C., Hawkinson, J.E., (1997) J. Med. Chem., 40, p. 73
- Anderson, A., Boyd, A.C., Byford, A., Campbell, A.C., Gemmell, D.K., Hamilton, N.M., Hill, D.R., Sundaram, H., (1997) J. Med. Chem., 40, p. 1668
- 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
- Burton, G., Galigniana, 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
- De Armas, P., Concepción, J.I., Francisco, C.G., Hernández, R., Salazar, J.A., Suárez, E., (1989) J. Chem. Soc., Perkin Trans. 1, p. 405
- Nicoletti, D., Ghini, A.A., Furtmuller, R., Sieghart, W., Dodd, R.H., Burton, G., (2000) Steroids, 65, p. 349
- Haasnoot, C.A.G., De Leew, F.A.A.M., Altona, C., (1980) Tetrahedron, 36, p. 2783
- Guinjoan, S.M., Golombek, D.A., Cardinali, D.P., (1992) Life Sci., 51, p. 2089
- Guinjoan, S.M., Golombek, D.A., Kanterewicz, B.I., Rosenstein, R.E., Cardinali, D.P., (1992) Neuroendocrinol. Lett., 14, p. 329
- Kokate, T.G., Svensson, B.E., Rogawski, M.A., (1994) J. Pharmacol. Exp. Ther., 270, p. 1223
- Vicent, G.P., Monteserín, M.C., Veleiro, A.S., Burton, G., Lantos, C.P., Galigniana, M.D., (1997) Mol. Pharmacol., 52, p. 749
- Harris, R.A., Allan, A.M., (1985) Science, 228, p. 1108
Citas:
---------- APA ----------
Veleiro, A.S., Rosenstein, R.E., Jaliffa, C.O., Grilli, M.L., Speroni, F. & Burton, G.
(2003)
. Synthesis and GABAA receptor activity of a 6,19-oxido analogue of pregnanolone. Bioorganic and Medicinal Chemistry Letters, 13(3), 343-346.
http://dx.doi.org/10.1016/S0960-894X(02)01019-3---------- CHICAGO ----------
Veleiro, A.S., Rosenstein, R.E., Jaliffa, C.O., Grilli, M.L., Speroni, F., Burton, G.
"Synthesis and GABAA receptor activity of a 6,19-oxido analogue of pregnanolone"
. Bioorganic and Medicinal Chemistry Letters 13, no. 3
(2003) : 343-346.
http://dx.doi.org/10.1016/S0960-894X(02)01019-3---------- MLA ----------
Veleiro, A.S., Rosenstein, R.E., Jaliffa, C.O., Grilli, M.L., Speroni, F., Burton, G.
"Synthesis and GABAA receptor activity of a 6,19-oxido analogue of pregnanolone"
. Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 3, 2003, pp. 343-346.
http://dx.doi.org/10.1016/S0960-894X(02)01019-3---------- VANCOUVER ----------
Veleiro, A.S., Rosenstein, R.E., Jaliffa, C.O., Grilli, M.L., Speroni, F., Burton, G. Synthesis and GABAA receptor activity of a 6,19-oxido analogue of pregnanolone. Bioorg. Med. Chem. Lett. 2003;13(3):343-346.
http://dx.doi.org/10.1016/S0960-894X(02)01019-3