Issue 15, 2007
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones†

Pablo H. Di Chenna,a   Adriana S. Veleiro,a   Juan M. Sonego,a   Nora R. Ceballos,b   M. Teresa Garland,c   Ricardo F. Baggiod  and  Gerardo Burton*a  

* Corresponding authors

a Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
E-mail: burton@qo.fcen.uba.ar
Fax: +54 11 4576-3385
Tel: +54 11 4576-3385

b Departamento de Biodiversidad y Biología Experimental, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina

c Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile y CIMAT, Av. Blanco Encalada 2008, Casilla 487–3, Santiago, Chile

d Departamento de Física, Comisión Nacional de Energía Atómica, Av. Gral. Paz 1499, B1650 San Martín, Pcia. de Buenos Aires, Argentina

Abstract

A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Δ4-3-keto steroids with a 19-mesylate in the presence of KOH in isopropanol. Three 6,19-cyclopregnanes were prepared (4, 5, 9); in the rat, 6,19-cycloprogesterone (4) and its 21-hydroxy derivative 5 displaced [3H]-dexamethasone from glucocorticoid receptors, the former compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors.

Graphical abstract: Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones

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Article information

DOI
https://doi.org/10.1039/B706828J
Article type
Paper
Submitted
08 May 2007
Accepted
04 Jun 2007
First published
26 Jun 2007

Org. Biomol. Chem., 2007,5, 2453-2457

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Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones

P. H. Di Chenna, A. S. Veleiro, J. M. Sonego, N. R. Ceballos, M. T. Garland, R. F. Baggio and G. Burton, Org. Biomol. Chem., 2007, 5, 2453 DOI: 10.1039/B706828J

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