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Abstract:

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.

Registro:

Documento: Artículo
Título:Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione
Autor:Veleiro, A.S.; Nevado, M.V.; Monteserín, M.C.; Burton, G.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Palabras clave:21-hydroxylation; oxido-bridged pregnanes; 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione; 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione; 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione; 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione; aldosterone; drug derivative; progesterone; 21 hydroxy 11,19 oxidopregn 4 ene 3,20 dione; 21 hydroxy 6,19 oxidopregn 4 ene 3,20 dione; deoxycorticosterone; mineralocorticoid receptor; unclassified drug; acetylation; article; chemical structure; chemistry; hydroxylation; oxidation reduction reaction; synthesis; drug structure; drug synthesis; steroidogenesis; Acetylation; Aldosterone; Hydroxylation; Molecular Structure; Oxidation-Reduction; Progesterone; Support, Non-U.S. Gov't
Año:1995
Volumen:60
Número:3
Página de inicio:268
Página de fin:271
DOI: http://dx.doi.org/10.1016/0039-128X(94)00052-E
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS: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
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v60_n3_p268_Veleiro

Referencias:

  • 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
  • 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
  • Galigniana, Vicent, Lantos, Burton, Ligand properties of 11,19-oxidoprogesterone (1993) A preliminary report, 81, pp. 333-340. , An Asoc Quim Argent
  • 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
  • Deghenghi, The synthesis of 19-oxygenated cardenolides. I. A convenient preparation of 19-hydroxydesoxycorticosterone (1966) J Org Chem, 31, pp. 2427-2429
  • 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
  • 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
  • Moriarty, Hu, Gupta, Direct α-hydroxylation of ketones using iodosobenzene (1981) Tetrahedron Letters, 22, pp. 1283-1286
  • Ringold, Stork, Steroids. XCIII. Introduction of the cortical hormone side-chain (1958) J Am Chem Soc, 80, p. 250

Citas:

---------- APA ----------
Veleiro, A.S., Nevado, M.V., Monteserín, M.C. & Burton, G. (1995) . Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione. Steroids, 60(3), 268-271.
http://dx.doi.org/10.1016/0039-128X(94)00052-E
---------- CHICAGO ----------
Veleiro, A.S., Nevado, M.V., Monteserín, M.C., Burton, G. "Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione" . Steroids 60, no. 3 (1995) : 268-271.
http://dx.doi.org/10.1016/0039-128X(94)00052-E
---------- MLA ----------
Veleiro, A.S., Nevado, M.V., Monteserín, M.C., Burton, G. "Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione" . Steroids, vol. 60, no. 3, 1995, pp. 268-271.
http://dx.doi.org/10.1016/0039-128X(94)00052-E
---------- VANCOUVER ----------
Veleiro, A.S., Nevado, M.V., Monteserín, M.C., Burton, G. Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione. Steroids. 1995;60(3):268-271.
http://dx.doi.org/10.1016/0039-128X(94)00052-E