In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins

Shigeki Sasaki, Katsunori Maruta, Hiroyuki Naito, Rie Maemura, Eiji Kawahara, Minoru Maeda

Research output: Contribution to journalArticle

13 Citations (Scopus)

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 languageEnglish
Pages (from-to)154-158
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume46
Issue number1
DOIs
Publication statusPublished - Jan 1 1998

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Acetogenins
Hydroxyl Radical
Lactones
Derivatives
Skeleton
Biological Products
Cells
Cell Line
In Vitro Techniques

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 journalArticle

Sasaki, Shigeki ; Maruta, Katsunori ; Naito, Hiroyuki ; Maemura, Rie ; Kawahara, Eiji ; Maeda, Minoru. / In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins. In: Chemical and Pharmaceutical Bulletin. 1998 ; Vol. 46, No. 1. pp. 154-158.
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