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On the relocation of the amino functionality to the ethyl side chain in aminoglutethimide: Synthesis and aromatase-inhibitory activity of 3-(2′-N,N-diethyl-amino)ethyl-3-phenylpiperidine-2,6-dione

Moniz, George A. ; Hammond, Gerald B.

Journal of heterocyclic chemistry, 1997-03, Vol.34 (2), p.649-652 [Periódico revisado por pares]

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Título:
On the relocation of the amino functionality to the ethyl side chain in aminoglutethimide: Synthesis and aromatase-inhibitory activity of 3-(2′-N,N-diethyl-amino)ethyl-3-phenylpiperidine-2,6-dione
Autor: Moniz, George A. ; Hammond, Gerald B.
É parte de: Journal of heterocyclic chemistry, 1997-03, Vol.34 (2), p.649-652
Notas: istex:0ACFE6C6DB8A9E29E1EC812B018354920066925A
Camille and Henry Dreyfus Foundation
ark:/67375/WNG-BTN7P48X-W
ArticleID:JHET5570340250
Henry Dreyfus Teacher‐Scholar 1996.
Descrição: Aminoglutethimide [3‐(4‐aminophenyl)‐3‐ethylpiperidine‐2,6‐dione] has been used clinically in the treatment of metastatic breast carcinoma. Inhibition of tumor growth is due to interference with estrogen biosynthesis. However, its action is not specific and its metabolism gives rise to toxic and non‐inhibitory metabolites. We sought to explore the impact of relocating the amino group in aminoglutethimide to the ethyl side chain. To that end, we now report the synthesis and aromatase‐inhibitory activity of 3‐(2′‐N,N‐diethylamino)ethyl‐3‐phenylpiperidine‐2,6‐dione 5. The introduction of the amino functionality on the ethyl group is accomplished via reductive animation of aldehyde 8, prepared in three steps from benzyl cyanide. The synthetic route presented can be used for the preparation of related derivatives of aminoglutethimide.
Editor: Hoboken: Wiley-Blackwell
Idioma: Inglês

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