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 | |
| Publication status | Published - 2001 |
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Keywords
- Antimalarial activity
- Febrifugine
- Structure-activity relationship
- Synthesis
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Chemistry(all)
- Pharmacology
Cite this
Synthesis and antimalarial activity of febrifugine derivatives. / Takeuchi, Yasuo; Koike, M.; Azuma, K.; Nishioka, Hiromi; Abe, H.; Kim, Hye-Sook; Wataya, Y.; Harayama, T.
In: Chemical and Pharmaceutical Bulletin, Vol. 49, No. 6, 2001, p. 721-725.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and antimalarial activity of febrifugine derivatives
AU - Takeuchi, Yasuo
AU - Koike, M.
AU - Azuma, K.
AU - Nishioka, Hiromi
AU - Abe, H.
AU - Kim, Hye-Sook
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
UR - http://www.scopus.com/inward/record.url?scp=0034962101&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034962101&partnerID=8YFLogxK
U2 - 10.1248/cpb.49.721
DO - 10.1248/cpb.49.721
M3 - Article
C2 - 11411524
AN - SCOPUS:0034962101
VL - 49
SP - 721
EP - 725
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 6
ER -