Synthesis and Antimalarial Activity of Febrifugine Derivatives

Yasuo TAKEUCHI; Midori KOIKE; Kumiko AZUMA; Hiromi NISHIOKA; Hitoshi ABE; Hye-Sook KIM; Yusuke WATAYA; Takashi HARAYAMA

doi:10.1248/cpb.49.721

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Synthesis and Antimalarial Activity of Febrifugine Derivatives

Yasuo TAKEUCHI, Midori KOIKE, Kumiko AZUMA, Hiromi NISHIOKA, Hitoshi ABE, Hye-Sook KIM, Yusuke WATAYA, Takashi HARAYAMA

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Keywords: antimalarial activity, febrifugine, synthesis, structure-activity relationship

JOURNAL FREE ACCESS

2001 Volume 49 Issue 6 Pages 721-725

DOI https://doi.org/10.1248/cpb.49.721

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Abstract

The regiosomers (2a, b) of the piperidine ring of febrifugine (1a) and isofebrifugine (1b) were synthesized from 4-allyl-3-piperidone (5). Reduction of 5 afforded a mixture of the trans and cis alcohols (6a, b) without diastereoselectivity; this result differentiated it from the reduction of 2-allyl-3-piperidone (14). The antimalarial activity of 2a, b and related compounds was tested.

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