Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione
The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido deriv...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
1995
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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 | 05716caa a22008657a 4500 | ||
|---|---|---|---|
| 001 | PAPER-12477 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204240.0 | ||
| 008 | 190411s1995 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0028985839 | |
| 024 | 7 | |2 cas |a aldosterone, 52-39-1, 6251-69-0; progesterone, 57-83-0; deoxycorticosterone, 64-85-7; 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione; 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione; Aldosterone, 52-39-1; Progesterone, 57-83-0 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a STEDA | ||
| 100 | 1 | |a Veleiro, A.S. | |
| 245 | 1 | 0 | |a Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione |
| 260 | |c 1995 | ||
| 270 | 1 | 0 | |m Burton, G.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Kamata, Matsui, Haga, Nakamura, Odaguchi, Itoh, Shimizu, Katoh, Aldosterone antagonists. 2. Synthesis and biological activities of 11,12-dehydropregnane derivatives (1987) J Med Chem, 30, pp. 1647-1658 | ||
| 504 | |a Brachet-Cota, Burton, An improved preparation of 11,19-oxidopregn-4-ene-3,20-dione and 6,19-oxidopregn-4-ene-3,11,20-trione (1990) Z Naturforsch [B], 45 b, pp. 711-715 | ||
| 504 | |a Galigniana, Vicent, Lantos, Burton, Ligand properties of 11,19-oxidoprogesterone (1993) A preliminary report, 81, pp. 333-340. , An Asoc Quim Argent | ||
| 504 | |a Kirk, Yeoh, New syntheses of 1921-dihydroxy-4-ene-320-dione 21-hydroxy-19-norpregn-4-ene-320-dione and 11β1921-trihydroxypregn-4-ene-320-dione (1983) Journal of the Chemical Society, Perkin Transactions 1, pp. 2945-2950 | ||
| 504 | |a Deghenghi, The synthesis of 19-oxygenated cardenolides. I. A convenient preparation of 19-hydroxydesoxycorticosterone (1966) J Org Chem, 31, pp. 2427-2429 | ||
| 504 | |a Moriarty, John, Du, Hypervalent iodine in organic synthesis (1981) A novel route to the dihydroxyacetone side chain in pregnene series, pp. 641-642. , J Chem Soc Chem Commun | ||
| 504 | |a Zemlicka, Beranek, Smrt, Preparation and methanolysis of uridine 6-azauridine and 6-azacytidine o-formyl derivatives (1962) Collection of Czechoslovak Chemical Communications, 27, pp. 2784-2795 | ||
| 504 | |a Moriarty, Hu, Gupta, Direct α-hydroxylation of ketones using iodosobenzene (1981) Tetrahedron Letters, 22, pp. 1283-1286 | ||
| 504 | |a Ringold, Stork, Steroids. XCIII. Introduction of the cortical hormone side-chain (1958) J Am Chem Soc, 80, p. 250 | ||
| 520 | 3 | |a The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido derivative, the hydroxylation was carried out on a precursor containing the oxido-bridge. This approach was not adequate for the 6,19-oxido steroid due to the very low yields encountered; hence in the latter case the order of introduction of the C-21 functionality and the oxido-bridge was reversed. © 1995. |l eng | |
| 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: We thank Universidad de Buenos Aires, and CONICET (Argentina) for financial support of this work. | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 21-HYDROXYLATION |
| 690 | 1 | 0 | |a OXIDO-BRIDGED PREGNANES |
| 690 | 1 | 0 | |a 21 HYDROXY 11,19 OXIDOPREGN 4 ENE 3,20 DIONE |
| 690 | 1 | 0 | |a 21 HYDROXY 6,19 OXIDOPREGN 4 ENE 3,20 DIONE |
| 690 | 1 | 0 | |a 21-HYDROXY-11,19-OXIDOPREGN-4-ENE-3,20-DIONE |
| 690 | 1 | 0 | |a 21-HYDROXY-6,19-OXIDOPREGN-4-ENE-3,20-DIONE |
| 690 | 1 | 0 | |a ALDOSTERONE |
| 690 | 1 | 0 | |a DRUG DERIVATIVE |
| 690 | 1 | 0 | |a PROGESTERONE |
| 690 | 1 | 0 | |a 21 HYDROXY 11,19 OXIDOPREGN 4 ENE 3,20 DIONE |
| 690 | 1 | 0 | |a 21 HYDROXY 6,19 OXIDOPREGN 4 ENE 3,20 DIONE |
| 690 | 1 | 0 | |a DEOXYCORTICOSTERONE |
| 690 | 1 | 0 | |a MINERALOCORTICOID RECEPTOR |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ACETYLATION |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a HYDROXYLATION |
| 690 | 1 | 0 | |a OXIDATION REDUCTION REACTION |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a STEROIDOGENESIS |
| 690 | 1 | 0 | |a ACETYLATION |
| 690 | 1 | 0 | |a ALDOSTERONE |
| 690 | 1 | 0 | |a HYDROXYLATION |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a OXIDATION-REDUCTION |
| 690 | 1 | 0 | |a PROGESTERONE |
| 690 | 1 | 0 | |a SUPPORT, NON-U.S. GOV'T |
| 700 | 1 | |a Nevado, M.V. | |
| 700 | 1 | |a Monteserín, M.C. | |
| 700 | 1 | |a Burton, G. | |
| 773 | 0 | |d 1995 |g v. 60 |h pp. 268-271 |k n. 3 |p Steroids |x 0039128X |w (AR-BaUEN)CENRE-577 |t Steroids | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0028985839&doi=10.1016%2f0039-128X%2894%2900052-E&partnerID=40&md5=ad1519046913a0a37fc08bacd51f4d61 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/0039-128X(94)00052-E |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_0039128X_v60_n3_p268_Veleiro |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v60_n3_p268_Veleiro |y Registro en la Biblioteca Digital |
| 961 | |a paper_0039128X_v60_n3_p268_Veleiro |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 73430 | ||