Abstract
We investigated the in vitro antitumor activities toward mouse and human cell lines of optically active synthetic bistetrahydrofuran (bis-THF) derivatives as analogs of Annonaceous acetogenins, which contain bis-THF, long unbranched alkyl chains, hydroxyl groups, and an α,β-unsaturated γ- lactone. These bis-THF derivatives were synthesized in a stereocontrolled manner, and have several modified structures at the alkyl side chains. We found that: 1) the unsaturated γ-lactone contributes to high potency in combination with the other less-functionalized alkyl chain, 2) the same absolute configuration of the bis-THF skeleton as that of the natural products produces more potent activity than the counterpart, 3) the alkyl chains and hydroxyl groups are crucial for exhibiting antitumor activity, 4) hydroxyl groups adjacent to the bis-THF skeleton may be replaced by amino or acylamino groups.
| Original language | English |
|---|---|
| Pages (from-to) | 154-158 |
| Number of pages | 5 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 46 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 1 1998 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Drug Discovery
Cite this
In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins. / Sasaki, Shigeki; Maruta, Katsunori; Naito, Hiroyuki; Maemura, Rie; Kawahara, Eiji; Maeda, Minoru.
In: Chemical and Pharmaceutical Bulletin, Vol. 46, No. 1, 01.01.1998, p. 154-158.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins
AU - Sasaki, Shigeki
AU - Maruta, Katsunori
AU - Naito, Hiroyuki
AU - Maemura, Rie
AU - Kawahara, Eiji
AU - Maeda, Minoru
PY - 1998/1/1
Y1 - 1998/1/1
N2 - We investigated the in vitro antitumor activities toward mouse and human cell lines of optically active synthetic bistetrahydrofuran (bis-THF) derivatives as analogs of Annonaceous acetogenins, which contain bis-THF, long unbranched alkyl chains, hydroxyl groups, and an α,β-unsaturated γ- lactone. These bis-THF derivatives were synthesized in a stereocontrolled manner, and have several modified structures at the alkyl side chains. We found that: 1) the unsaturated γ-lactone contributes to high potency in combination with the other less-functionalized alkyl chain, 2) the same absolute configuration of the bis-THF skeleton as that of the natural products produces more potent activity than the counterpart, 3) the alkyl chains and hydroxyl groups are crucial for exhibiting antitumor activity, 4) hydroxyl groups adjacent to the bis-THF skeleton may be replaced by amino or acylamino groups.
AB - We investigated the in vitro antitumor activities toward mouse and human cell lines of optically active synthetic bistetrahydrofuran (bis-THF) derivatives as analogs of Annonaceous acetogenins, which contain bis-THF, long unbranched alkyl chains, hydroxyl groups, and an α,β-unsaturated γ- lactone. These bis-THF derivatives were synthesized in a stereocontrolled manner, and have several modified structures at the alkyl side chains. We found that: 1) the unsaturated γ-lactone contributes to high potency in combination with the other less-functionalized alkyl chain, 2) the same absolute configuration of the bis-THF skeleton as that of the natural products produces more potent activity than the counterpart, 3) the alkyl chains and hydroxyl groups are crucial for exhibiting antitumor activity, 4) hydroxyl groups adjacent to the bis-THF skeleton may be replaced by amino or acylamino groups.
UR - http://www.scopus.com/inward/record.url?scp=0031935519&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031935519&partnerID=8YFLogxK
U2 - 10.1248/cpb.46.154
DO - 10.1248/cpb.46.154
M3 - Article
C2 - 9468648
AN - SCOPUS:0031935519
VL - 46
SP - 154
EP - 158
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 1
ER -