Synthesis and antimalarial activity of febrifugine derivatives

Y. Takeuchi; M. Koike; K. Azuma; H. Nishioka; H. Abe; H. S. Kim; Y. Wataya; T. Harayama

doi:10.1248/cpb.49.721

Synthesis and antimalarial activity of febrifugine derivatives

Y. Takeuchi, M. Koike, K. Azuma, H. Nishioka, H. Abe, H. S. Kim, Y. Wataya, T. Harayama

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

The regioisomers (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 di-activity of 2a,b and related compounds was tested.

Original language	English
Pages (from-to)	721-725
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	49
Issue number	6
DOIs	https://doi.org/10.1248/cpb.49.721
Publication status	Published - 2001

Keywords

Antimalarial activity
Febrifugine
Structure-activity relationship
Synthesis

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.49.721

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abstract = "The regioisomers (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 di-activity of 2a,b and related compounds was tested.",

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T1 - Synthesis and antimalarial activity of febrifugine derivatives

AU - Takeuchi, Y.

AU - Koike, M.

AU - Azuma, K.

AU - Nishioka, H.

AU - Abe, H.

AU - Kim, H. S.

AU - Wataya, Y.

AU - Harayama, T.

PY - 2001

Y1 - 2001

N2 - The regioisomers (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 di-activity of 2a,b and related compounds was tested.

AB - The regioisomers (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 di-activity of 2a,b and related compounds was tested.

KW - Antimalarial activity

KW - Febrifugine

KW - Structure-activity relationship

KW - Synthesis

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Synthesis and antimalarial activity of febrifugine derivatives

Abstract

Keywords

ASJC Scopus subject areas

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