書誌事項
- タイトル別名
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- Total Synthesis and Structure-activity Relationship of a Cytotoxic Polycyclic Ether Gymnocin-A
- サイボウ ドクセイ ポリエーテル Gymnocin A ノ ゼンゴウセイ ト コウゾウ カッセイ ソウカン
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抄録
Gymnocin-A is a polycyclic ether toxin, isolated from the notorious red tide dinoflagellate, Karenia mikimotoi. Structurally, it is characterized by 14 contiguous and saturated ether rings and a 2-methyl-2-butenal side chain. The toxin is a rare polycyclic ether natural product that exhibits cytotoxicity against P 388 murine leukemia (IC50=1.3 μg/mL); however, the biological mechanism of action remains unknown to date. We have accomplished a highly convergent and efficient total synthesis of gymnocin-A by using our developed B-alkyl Suzuki-Miyaura coupling-based methodology. The convergent nature of our synthesis is well suited for preparation of various structural analogues of gymnocin-A to explore the structure-activity relationship (SAR). The results of SAR studies indicated that an α, β-unsaturated aldehyde functionality of the side chain and the molecular length of the polycyclic ether skeleton were the crucial structural elements required for cytotoxicity.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 64 (8), 808-818, 2006
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680289594624
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- NII論文ID
- 10017652125
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 8060021
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- 抄録ライセンスフラグ
- 使用不可