PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids
Reaction of 11-pregnene-3,20-dione (6) or 3-α-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of ea...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2003
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 08232caa a22011537a 4500 | ||
|---|---|---|---|
| 001 | PAPER-5056 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203441.0 | ||
| 008 | 190411s2003 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037429092 | |
| 024 | 7 | |2 cas |a eltanolone, 128-20-1 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TETRA | ||
| 100 | 1 | |a Di Chenna, P.H. | |
| 245 | 1 | 0 | |a PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| 260 | |c 2003 | ||
| 270 | 1 | 0 | |m Dodd, R.H.; Inst. de Chim. des Substances N., CNRS, 91198 Gif-sur-Yvette Cedex, France; email: robert.dodd@icsn.cnrs-gif.fr |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Hamilton, N.M., (2002) Curr. Top. Med. Chem., 2, pp. 887-902 | ||
| 504 | |a Phillipps, G.H., Ayres, B.E., Bailey, E.J., Ewan, G.B., Looker, B.E., May, P.J., (1979) J. Steroid Biochem., 11, pp. 79-86 | ||
| 504 | |a 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, pp. 1668-1681 | ||
| 504 | |a Njar, V.C.O., Hector, M., Hartmann, R.W., (1996) Bioorg. Med. Chem., 4, pp. 1447-1453 | ||
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| 504 | |a Ling, Y., Li, J., Kato, K., Liu, Y., Wang, X., Klus, G.T., Marat, K., Brodie, A.M.H., (1998) Bioorg. Med. Chem., 6, pp. 1683-1693 | ||
| 504 | |a Njar, V.C.O., Safi, E., Silverton, J.V., Robinson, C.H., (1993) J. Chem. Soc., Perkin Trans. 1, pp. 1161-1168 | ||
| 504 | |a Fioravanti, S., Pellacani, L., Tabanella, S., Tardella, P.A., (1998) Tetrahedron, 54, pp. 14105-14112 | ||
| 504 | |a Njar, V.C.O., Hartmann, R.W., Robinson, C.H., (1995) J. Chem. Soc., Perkin Trans. 1, pp. 985-991 | ||
| 504 | |a Tzikas, A., Tamm, C., Boller, A., Fürst, A., (1976) Helv. Chem. Acta, 59, pp. 1850-1866 | ||
| 504 | |a Evans, D.A., Faul, M.M., Bilodeau, M.T., (1994) J. Am. Chem. Soc., 116, pp. 2742-2753 | ||
| 504 | |a Dauban, P., Dodd, R.H., (1998) Tetrahedron Lett., 39, pp. 5739-5742 | ||
| 504 | |a Müller, P., (1997) Advances in Catalytic Processes, 2, pp. 113-151. , For a review on transition metal-catalyzed nitrene transfer reactions, see: Doyle M.P. Greenwich, CT: JAI | ||
| 504 | |a Hudlicky, T., Tian, X., Königsberger, K., Maurya, R., Rouden, J., Fan, B., (1996) J. Am. Chem. Soc., 118, pp. 10752-10765 | ||
| 504 | |a Wuts, P.G.M., Northuis, J.M., (1998) Tetrahedron Lett., 39, pp. 3889-3890 | ||
| 504 | |a Alonso, D.A., Andersson, P.G., (1998) J. Org. Chem., 63, pp. 9455-9461 | ||
| 504 | |a Dauban, P., Dodd, R.H., (1999) J. Org. Chem., 64, pp. 5304-5307 | ||
| 504 | |a Di Chenna, P.H., Dauban, P., Ghini, A., Burton, G., Dodd, R.H., (2000) Tetrahedron Lett., 41, pp. 7041-7045. , A preliminary report of these studies has appeared. See: | ||
| 504 | |a The atomic coordinates for compound 9 have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 1889952. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; Tschesche, R., Hombach, R., Scholten, H., Peters, M., (1970) Phytochemistry, 9, pp. 1505-1515 | ||
| 504 | |a Liang, J.-L., Yu, X.-Q., Che, C.-M., (2002) J. Chem. Soc., Chem. Commun., pp. 124-125 | ||
| 504 | |a Sheldrick, G.M., (1997) SHELXS-97. Program for Structure Resolution, , University of Göttingen: Germany | ||
| 504 | |a Sheldrick, G.M., (1997) SHELXL-97. Program for Structure Refinement, , University of Göttingen: Germany | ||
| 504 | |a Sheldrick, G.M., (1994) SHELXTL-PC, Version 5.0; Siemens Analytical X-ray Instruments, Inc., , Madison, Wisconsin, USA | ||
| 520 | 3 | |a Reaction of 11-pregnene-3,20-dione (6) or 3-α-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11α,12α-N-methyl aziridinosteroids 9 and 15, respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone (1). © 2003 Elsevier Science Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Andes-C13575, CONICYT-FONDAP 11980002 | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: ARC Centre of Excellence in Cognition and its Disorders, CCD | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: We thank ECOS, France (grant A97 E06), Universidad de Buenos Aires and Agencia Nacional de Promoción Cientı́fica y Tecnólogica (Argentina) for financial support and Fundación Andes-C13575 and CONICYT-FONDAP 11980002 for the purchase of a CCD detector. | ||
| 593 | |a Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 593 | |a Inst. de Chim. des Substances N., CNRS, 91198 Gif-sur-Yvette Cedex, France | ||
| 593 | |a Departamento de Física, Comn. Nac. de Energia Atómica, Av. del Libertador 8250, C1429 Buenos Aires, Argentina | ||
| 593 | |a Departamento de Física, Fac. de Cie. Fis. y Matemat., Universidad de Chile, Av. Blanco Encalada 2008, Casilla 487-3 Santiago, Chile | ||
| 690 | 1 | 0 | |a AZIRIDINE |
| 690 | 1 | 0 | |a IMINOIODINANE |
| 690 | 1 | 0 | |a SES GROUP |
| 690 | 1 | 0 | |a STEROID |
| 690 | 1 | 0 | |a 3ALPHA ACETOXY 5BETA H 11 PREGNEN 20 ONE |
| 690 | 1 | 0 | |a 3ALPHA ACETOXY N [2 (TRIMETHYLSILYL)ETHANESULFONYL] 11ALPHA,12ALPHA AZIRIDINO 5BETA H PREGNAN 20 ONE |
| 690 | 1 | 0 | |a 3ALPHA HYDROXY N METHYL 11ALPHA,12ALPHA AZIRIDINO 5BETA H PREGNAN 20 ONE |
| 690 | 1 | 0 | |a ALKANE DERIVATIVE |
| 690 | 1 | 0 | |a AZIRIDINE DERIVATIVE |
| 690 | 1 | 0 | |a COPPER DERIVATIVE |
| 690 | 1 | 0 | |a ELTANOLONE |
| 690 | 1 | 0 | |a IODINE DERIVATIVE |
| 690 | 1 | 0 | |a KETONE DERIVATIVE |
| 690 | 1 | 0 | |a N [2 (TRIMETHYLSILYL)ETHANESULFONYL] 11ALPHA,12ALPHA AZIRIDINO 5BETA H PREGNANE 3,20 DIONE |
| 690 | 1 | 0 | |a N METHYL 11ALPHA,12ALPHA AZIRIDINO 5BETA H PREGNANE 3,20 DIONE |
| 690 | 1 | 0 | |a NEUROSTEROID |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a TRIMETHYLSILYL DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a AZIRIDINATION |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a DRUG CONFORMATION |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a METHYLATION |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a PROTON NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a X RAY CRYSTALLOGRAPHY |
| 700 | 1 | |a Dauban, P. | |
| 700 | 1 | |a Ghini, A. | |
| 700 | 1 | |a Baggio, R. | |
| 700 | 1 | |a Garland, M.T. | |
| 700 | 1 | |a Burton, G. | |
| 700 | 1 | |a Dodd, R.H. | |
| 773 | 0 | |d 2003 |g v. 59 |h pp. 1009-1014 |k n. 7 |p Tetrahedron |x 00404020 |w (AR-BaUEN)CENRE-45 |t Tetrahedron | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/S0040-4020(02)01655-1 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404020_v59_n7_p1009_DiChenna |y Handle |
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