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Abstract:

18-Hydroxy-6,19-oxidoprogesterone and 18-hydroxy-11,19- oxidoprogesterone were synthesized from readily available materials. The functionalization of C-18 was accomplished with phenyliodosodiacetate/iodine, whereas that of C-19 was carried out with the mercuric oxide/iodine system, both under irradiation with visible light. For 18-hydroxy-11,19-oxidoprogesterone, C-19 was functionalized before C-18, whereas the reverse order had to be used for the 6,19-oxido derivative.

Registro:

Documento: Artículo
Título:Synthesis of oxido-bridged analogs of 18-hydroxyprogesterone
Autor:Benedetti Doctorovich, M.O.V.; Ghini, A.A.; Burton, G.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Palabras clave:18-hydroxypregnanes; oxido-bridged pregnanes; 18 hydroxy 11,19 oxidoprogesterone; 18 hydroxy 6,19 oxidoprogesterone; progesterone derivative; unclassified drug; article; carbon nuclear magnetic resonance; drug synthesis; irradiation; proton nuclear magnetic resonance; steroidogenesis
Año:1996
Volumen:61
Número:6
Página de inicio:345
Página de fin:348
DOI: http://dx.doi.org/10.1016/0039-128X(96)00034-7
Título revista:Steroids
Título revista abreviado:STEROIDS
ISSN:0039128X
CODEN:STEDA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v61_n6_p345_BenedettiDoctorovich

Referencias:

  • Burton, G., Galigniana, M., De Lavallaz, S., Brachet-Cota, A.L., Sproviero, E.M., Ghini, A.A., Lantos, C.P., Damasco, M.C., Sodium retaining activity of some natural and synthetic 21-deoxysteroids (1995) Mol Pharmacol, 47, pp. 535-543
  • Yamakawa, M., Ezumi, K., Shiro, M., Nakai, H., Kamata, S., Matsui, T., Haga, N., Relationships of the molecular structure of aldosterone derivatives with their binding affinity for mineralocorticoid receptor (1986) Mol Pharmacol, 30, pp. 585-589
  • Veleiro, A.S., Nevado, M.V., Monteserin, 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 (1995) Steroids, 60, pp. 268-271
  • Edwards, R.W.H., The paper chromatography of steroids esters (1963) J Chromatogr, 12, pp. 212-218
  • De Armas, P., Concepción, J.I., Francisco, C.G., Hernández, R., Salazar, J.A., Suarez, E., Intramolecular hydrogen abstraction. Hypervalent organoiodine compounds, convenient reagents for alkoxyl radical generation (1989) J Chem Soc (Perkin 1), pp. 405-411
  • Benedetti, M.O.V., Burton, G., Improved preparation of 18-hydroxyprogesterone (1992) Org Prep Proc Int, 24, pp. 701-704
  • Burke, S.D., Silks, L.A., Strickland, S.M.S., Remote functionalization and molecular modelling. Observations relevant to the Barton and hypoiodite reactions (1988) Tetrahedron Lett, 29, pp. 2761-2764
  • Brachet-Cota, A.L., Burton, G., 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
  • Ferrara, A., Benedetti, M.O.V., Ghini, A.A., Burton, G., 17(13 → 18)-aboeo-Pregnanes. Synthesis of progesterone analogues (1993) J Chem Res (S), pp. 276-277

Citas:

---------- APA ----------
Benedetti Doctorovich, M.O.V., Ghini, A.A. & Burton, G. (1996) . Synthesis of oxido-bridged analogs of 18-hydroxyprogesterone. Steroids, 61(6), 345-348.
http://dx.doi.org/10.1016/0039-128X(96)00034-7
---------- CHICAGO ----------
Benedetti Doctorovich, M.O.V., Ghini, A.A., Burton, G. "Synthesis of oxido-bridged analogs of 18-hydroxyprogesterone" . Steroids 61, no. 6 (1996) : 345-348.
http://dx.doi.org/10.1016/0039-128X(96)00034-7
---------- MLA ----------
Benedetti Doctorovich, M.O.V., Ghini, A.A., Burton, G. "Synthesis of oxido-bridged analogs of 18-hydroxyprogesterone" . Steroids, vol. 61, no. 6, 1996, pp. 345-348.
http://dx.doi.org/10.1016/0039-128X(96)00034-7
---------- VANCOUVER ----------
Benedetti Doctorovich, M.O.V., Ghini, A.A., Burton, G. Synthesis of oxido-bridged analogs of 18-hydroxyprogesterone. STEROIDS. 1996;61(6):345-348.
http://dx.doi.org/10.1016/0039-128X(96)00034-7