Synthesis and biological activity of enantiomeric pairs of 5-(alk-2-enyl)thiolactomycin and 5-〔(E)-cycloalk-2-enylidenemethyl〕thiolactomycin congeners
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- Ohata Kohei
- Discovery Research Laboratories, Kyorin Pharmaceutical Co., Ltd.
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- Terashima Shiro
- Sagami Chemical Research Center
書誌事項
- タイトル別名
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- Synthesis and Biological Activity of Enantiomeric Pairs of 5-(Alk-2-enyl)thiolactomycin and 5-[(E)-Cycloalk-2-enylidenemethyl]thiolactomycin Congeners
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The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure–activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2-enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 57 (9), 920-936, 2009
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679145203456
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- NII論文ID
- 130000124187
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 10332545
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
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- 使用不可