Synthesis and GABAA receptor activity of a 6,19-oxido analogue of pregnanolone

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 3, 2003, Pages 343-346

  Veleiro, Adriana S ^a   Rosenstein, Ruth E ^b   Jaliffa, Carolina O ^b   Grilli, María L ^b   Speroni, Florencia ^a   Burton, Gerardo ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

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;

EID: 0037325551     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)01019-3     Document Type: Article

References (26)

1. Sieghart W. Pharmacol. Rev. 47:1995;182.
2. Baulieu E.E. Psychoneuroendocrinol. 23:1998;963.
3. Baulieu E.E. Recent Prog. Horm. Res. 52:1997;1.
4. Compagnone N.A., Mellon S.H. Front. Neuroendocrinol. 21:2000;1.
5. Tsutsui K., Ukena K., Usui M., Sakamoto H., Takase M. Neurosci. Res. 36:2000;261.
6. Gasior M., Carter R.B., Witkin J.M. Trends Pharmacol. Sci. 20:1999;107.
7. Lambert J.J., Belelli D., Hill-Venning C., Peters J.A. Trends Pharmacol. Sci. 16:1995;295.
8. Belelli D., Lan N.C., Gee K.W. Neurosci. Biobehav. Rev. 14:1990;315.
9. Golombek D.A., Fernández D.D., De Brito Sánchez M.G., Burin L., Cardinali D.P. Eur. J. Pharmacol. 210:1991;253.
10. Rogawski M.A., Reddy D.S. Int. Rev. Neurobiol. 49:2002;199.
11. Beekman M., Ungard J.T., Gasior M., Carter R.B., Dijkstra D., Golberg S.R., Witkin J.M. J. Pharmacol. Exp. Ther. 284:1998;868.
12. Upasani R.B., Yang K.C., Acosta-Burruel M., Konkoy C.S., McLellan J.A., Woodward R.M., Lan N.C., Carter R.B., Hawkinson J.E. J. Med. Chem. 40:1997;73.
13. Anderson A., Boyd A.C., Byford A., Campbell A.C., Gemmell D.K., Hamilton N.M., Hill D.R., Hill-Venning C., Lambert J.J., Maidment M.S., May V., Marshall R.J., Peters J.A., Rees D.C., Stevenson D., Sundaram H. J. Med. Chem. 40:1997;1668.
14. Anderson A., Boyd A.C., Clark J.K., Fielding L., Gemmell D.K., Hamilton N.M., Maidment M.S., May V., McGuire R., McPhail P., Sansbury F.H., Sundaram H., Taylor R. J. Med. Chem. 43:2000;4118.
15. Burton G., Galigniana M.D., de Lavallaz S., Brachet-Cota A.L., Sproviero E.M., Ghini A.A., Lantos C.P., Damasco M.C. Mol. Pharmacol. 47:1995;535.
16. Semiempirical AM1 calculations and RMS fitting of structures were performed with Hyperchem 7.0 (Hypercube Inc., USA).
17. de Armas P., Concepción J.I., Francisco C.G., Hernández R., Salazar J.A., Suárez E. J. Chem. Soc., Perkin Trans. 1. 1989;405.
18. Nicoletti D., Ghini A.A., Furtmuller R., Sieghart W., Dodd R.H., Burton G. Steroids. 65:2000;349.
19. 3 requires C, 76.3; H, 9.2%).
20. Haasnoot C.A.G., de Leew F.A.A.M., Altona C. Tetrahedron. 36:1980;2783.
21. Animals and drugs. Male adult Syrian hamsters (Mesocricetus auratus, 80-140 g) were raised in our colony, under a 14 h light - 10 h dark photoperiod, with lights on at 6:00 h. Hamsters were given access to food and water ad libitum. All drugs were from Sigma Chemical Co. (St. Louis, MO).
22. Guinjoan S.M., Golombek D.A., Cardinali D.P. Life Sci. 51:1992;2089.
23. Guinjoan S.M., Golombek D.A., Kanterewicz B.I., Rosenstein R.E., Cardinali D.P. Neuroendocrinol. Lett. 14:1992;329.
24. Kokate T.G., Svensson B.E., Rogawski M.A. J. Pharmacol. Exp. Ther. 270:1994;1223.
25. Vicent G.P., Monteserín M.C., Veleiro A.S., Burton G., Lantos C.P., Galigniana M.D. Mol. Pharmacol. 52:1997;749.
26. Harris R.A., Allan A.M. Science. 228:1985;1108.