Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulfone derivatives. The trans stereochemistry at the A/B ring jun...
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2006
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 06491caa a22010337a 4500 | ||
|---|---|---|---|
| 001 | PAPER-7177 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203655.0 | ||
| 008 | 190411s2006 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-33646074526 | |
| 024 | 7 | |2 cas |a 3alpha hydroxy 5alpha pregnan 20 one, 516-54-1; sulfoxide, 120-62-7 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TETRA | ||
| 100 | 1 | |a Durán, F.J. | |
| 245 | 1 | 0 | |a Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone |
| 260 | |c 2006 | ||
| 270 | 1 | 0 | |m Burton, G.; Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina; email: burton@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Gasior, M., Carter, R.B., Witkin, J.M., (1999) Trends Pharmacol. Sci., 20, pp. 107-112 | ||
| 504 | |a Hamilton, N.M., (2002) Curr. Top. Med. Chem., 2, pp. 887-902 | ||
| 504 | |a Beekman, M., Ungard, J.T., Gasior, M., Carter, R.B., Dijkstra, D., Goldberg, S.R., Witkin, J.M., (1998) J. Pharmacol. Exp. Ther., 284, pp. 868-877 | ||
| 504 | |a Nicoletti, D., Ghini, A.A., Furtmüller, R., Sieghart, W., Dodd, R.H., Burton, G., (2000) Steroids, 65, pp. 349-356. , and references cited therein | ||
| 504 | |a Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G., (1995) J. Chem. Soc., Perkin Trans. 1, pp. 1089-1093 | ||
| 504 | |a Nicoletti, D., Ghini, A.A., Burton, G., (1996) J. Org. Chem., 61, pp. 6673-6677 | ||
| 504 | |a Kasal, A., Matyas, L., Budesinsky, M., (2005) Tetrahedron, 61, pp. 2269-2278 | ||
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| 504 | |a Speckamp, W.N., Kesselaar, H., (1974) Tetrahedron Lett., 38, pp. 3405-3408 | ||
| 504 | |a Back, T.G., Baron, D.L., Morzycki, J.W., (1994) Heterocycles, 38, pp. 1053-1060 | ||
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| 504 | |a Kirbi, A.J., (1983) The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, , See for example, Springer, Berlin p 23 | ||
| 504 | |a Gee, K.W., Bolger, M.B., Brinton, R.E., Coirini, H., McEwen, B.S., (1988) J. Pharmacol. Exp. Ther., 246, pp. 803-812 | ||
| 504 | |a Trost, B.M., Curran, D.P., (1981) Tetrahedron Lett., 22, pp. 1287-1291 | ||
| 504 | |a Zemlicka, J., Beranek, J., Smrt, J., (1962) Collect. Czech. Chem. Commun., 27, pp. 2784-2795 | ||
| 504 | |a Bradford, M.M., (1976) Anal. Biochem., 72, pp. 248-254 | ||
| 504 | |a Rodbard, D., Lewalds, J.E., (1979) Computer Analysis of Radioligand Assay and Radioimmunoassay Data, pp. 79-103. , Diczfalusi E. (Ed), Karolinska Institute, Stockholm | ||
| 504 | |a Gonzalez, S.L., Ferrini, M., Coirini, H., Gonzalez-Deniselle, M.C., De Nicola, A.F., (1992) Brain Res., 589, pp. 97-101 | ||
| 520 | 3 | |a A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulfone derivatives. The trans stereochemistry at the A/B ring junction was accomplished by stereoselective reduction of an intermediate hemithioketal with triethylsilane/BF3·Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABAA receptor activity comparable to allopregnanolone. © 2006 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 10962 | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: This work was supported by grants from Agencia Nacional de Promoción Científica y Tecnológica (PICT 10962), CONICET (Argentina) and Universidad de Buenos Aires. | ||
| 593 | |a Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina | ||
| 593 | |a Instituto de Biología y Medicina Experimental (CONICET), Vuelta de Obligado 2490, C1428ADN Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 6-THIASTEROIDS |
| 690 | 1 | 0 | |a ALLOPREGNANOLONE |
| 690 | 1 | 0 | |a GABAA RECEPTOR |
| 690 | 1 | 0 | |a NEUROSTEROID ANALOGS |
| 690 | 1 | 0 | |a S,S-DIOXO-THIASTEROIDS |
| 690 | 1 | 0 | |a S-OXO-THIASTEROIDS |
| 690 | 1 | 0 | |a 3ALPHA BENZYLOXY 19 HYDROXY 6 THIA 5ALPHA PREGNAN 20 ONE |
| 690 | 1 | 0 | |a 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE |
| 690 | 1 | 0 | |a 3ALPHA HYDROXY 6 THIA 5ALPHA PREGNAN 20 ONE |
| 690 | 1 | 0 | |a 3BETA HYDROXY 19 FORMYLOXY 6 THIA 5ALPHA PREGNAN 20 ONE |
| 690 | 1 | 0 | |a NEUROSTEROID |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a SULFONE DERIVATIVE |
| 690 | 1 | 0 | |a SULFOXIDE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANALYTIC METHOD |
| 690 | 1 | 0 | |a ANIMAL TISSUE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL BOND |
| 690 | 1 | 0 | |a CHEMICAL PROCEDURES |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DRUG RECEPTOR BINDING |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a LIGAND BINDING |
| 690 | 1 | 0 | |a MALE |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a RAT |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a ANIMALIA |
| 690 | 1 | 0 | |a THIA |
| 700 | 1 | |a Ghini, A.A. | |
| 700 | 1 | |a Coirini, H. | |
| 700 | 1 | |a Burton, G. | |
| 773 | 0 | |d 2006 |g v. 62 |h pp. 4762-4768 |k n. 20 |p Tetrahedron |x 00404020 |w (AR-BaUEN)CENRE-45 |t Tetrahedron | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/j.tet.2006.03.025 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404020_v62_n20_p4762_Duran |y Handle |
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