Synthesis of novel 6-aza-B- and 11-aza-C-homoestranes as antifertility agents
Reaction of 3,9α,17β-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether (3) with N 3HBF 3 etherate leads mainly to lactam (4) along with the N-azido compound (5) as a minor product. Under similar conditions, 3,17β-dihydroxyestra-1,3,5(10)-trien-6-one 17-acetate 3-methyl ether gives la...
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Veröffentlicht in: | Steroids 1993-02, Vol.58 (2), p.69-73 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Reaction of 3,9α,17β-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether
(3) with N
3HBF
3 etherate leads mainly to lactam
(4) along with the N-azido compound
(5) as a minor product. Under similar conditions, 3,17β-dihydroxyestra-1,3,5(10)-trien-6-one 17-acetate 3-methyl ether gives lactam
(12) and the tetrazolo derivative
(9). Similar reaction of the diacetate
(8) gives only the tetrazole derivative
(11). Compounds
4, 6, and
10 prevent implantation in rats at 5-, 10-, and 5-mg/kg doses, respectively. Compounds
4,6,9, and
10 show significant estrogenic activity at the respective contraceptive doses. (Steroids
58:69–73, 1993) |
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ISSN: | 0039-128X 1878-5867 |
DOI: | 10.1016/0039-128X(93)90055-R |