Synthesis of 6,19-sulfamidate bridged pregnanes
Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cy...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2005
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 07227caa a22011057a 4500 | ||
|---|---|---|---|
| 001 | PAPER-3904 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203323.0 | ||
| 008 | 190411s2005 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-26844505734 | |
| 024 | 7 | |2 cas |a acetic acid, 127-08-2, 127-09-3, 64-19-7, 71-50-1; cyanide, 57-12-5; fluoride, 16984-48-8; sulfanilamide, 34612-79-8, 6101-31-1, 63-74-1; Bridged Compounds; Pregnanes; Sulfonic Acids | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JOCEA | ||
| 100 | 1 | |a Duran, F.J. | |
| 245 | 1 | 0 | |a Synthesis of 6,19-sulfamidate bridged pregnanes |
| 260 | |c 2005 | ||
| 270 | 1 | 0 | |m Burton, G.; Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina; email: burton@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Smith, S.S., (2003) Neurosteroid Effects in the Central Nervous System: The Role of the GABA-A Receptor, , Ed.; CRC Press: Boca Raton | ||
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| 504 | |a Stone, T.W., (1996) CNS Neurotransmitters and Neuromodulators. Neuroactive Steroids, , Ed.; CRC Press: Boca Raton, Chapters 2 and 4 | ||
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| 504 | |a note; Gee, K.W., Bolger, M.B., Brinton, R.E., Coirini, H., McEwen, B.S., (1988) J. Pharmacol. Exp. Ther., 246, pp. 803-812 | ||
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| 504 | |a note | ||
| 520 | 3 | |a Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cyanide, fluoride, and acetate. In the isolated case of acetate, a reversal of regioselectivity was observed at higher temperatures, a result attributed to a rearrangement process involving aziridine ring opening at the C-5 position and subsequent migration of the acetyl meiety to C-6. © 2005 American Chemical Society. |l eng | |
| 593 | |a Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina | ||
| 593 | |a Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, F-91198 Gif-sur-Yvette Cedex, France | ||
| 690 | 1 | 0 | |a ADDITION REACTIONS |
| 690 | 1 | 0 | |a CONFORMATIONS |
| 690 | 1 | 0 | |a RING OPENING POLYMERIZATION |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a SUBSTITUTION REACTIONS |
| 690 | 1 | 0 | |a SULFUR COMPOUNDS |
| 690 | 1 | 0 | |a 6,9-SULFAMIDATE BRIDGED PREGNANES |
| 690 | 1 | 0 | |a NITRENE |
| 690 | 1 | 0 | |a NUCLEOPHILIC RING OPENING |
| 690 | 1 | 0 | |a REGIOSELECTIVITY |
| 690 | 1 | 0 | |a AROMATIC COMPOUNDS |
| 690 | 1 | 0 | |a 4 AMINOBUTYRIC ACID A RECEPTOR |
| 690 | 1 | 0 | |a ACETIC ACID |
| 690 | 1 | 0 | |a AZIRIDINE DERIVATIVE |
| 690 | 1 | 0 | |a CYANIDE |
| 690 | 1 | 0 | |a FLUORIDE |
| 690 | 1 | 0 | |a NEUROSTEROID |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a SULFANILAMIDE |
| 690 | 1 | 0 | |a ANTICONVULSANT ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a CONFORMATIONAL TRANSITION |
| 690 | 1 | 0 | |a DERIVATIZATION |
| 690 | 1 | 0 | |a MOLECULAR INTERACTION |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a RING OPENING |
| 690 | 1 | 0 | |a SOLUBILITY |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a BRIDGED COMPOUNDS |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a PREGNANES |
| 690 | 1 | 0 | |a SULFONIC ACIDS |
| 700 | 1 | |a Ghini, A.A. | |
| 700 | 1 | |a Dauban, P. | |
| 700 | 1 | |a Dodd, R.H. | |
| 700 | 1 | |a Burton, G. | |
| 773 | 0 | |d 2005 |g v. 70 |h pp. 8613-8616 |k n. 21 |p J. Org. Chem. |x 00223263 |w (AR-BaUEN)CENRE-337 |t Journal of Organic Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1021/jo051290a |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00223263_v70_n21_p8613_Duran |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v70_n21_p8613_Duran |y Registro en la Biblioteca Digital |
| 961 | |a paper_00223263_v70_n21_p8613_Duran |b paper |c PE | ||
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