Total Synthesis of Phaeosphaerides with STAT3 Inhibitory Activity
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- Kobayashi Kenichi
- School of Pharmaceutical Sciences, Health Sciences University of Hokkaido Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University
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- Kogen Hiroshi
- Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University
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- Tamura Osamu
- Showa Pharmaceutical University
Bibliographic Information
- Other Title
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- STAT3阻害活性を有するPhaeosphaeride類の全合成
- STAT3 ソガイ カッセイ オ ユウスル Phaeosphaerideルイ ノ ゼン ゴウセイ
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Abstract
<p>Phaeosphaeride A was originally isolated from the endophyte FA39 as an inhibitor of STAT3-DNA binding along with its inactive diastereomer phaeosphaeride B. Among proteins in the STAT (signal transducer and activator of transcription) family, STAT3 plays a crucial role in various cellular processes, including cell proliferation, survival, and differentiation. STAT3 could be a potential target for molecular-targeted cancer therapy because it is constantly activated in most solid tumors. Therefore, the STAT3 inhibitor phaeosphaeride A has been recognized as a promising seed compound for anticancer drug development.</p><p>After its isolation in 2006, our and other groups’ longstanding synthetic efforts toward phaeosphaeride A resulted in the total synthesis and structural revision of the natural product, which was subsequently confirmed by X-ray crystal structure analysis. In addition, a biomimetic acid-mediated transformation of phaeosphaeride A to phaeosphaeride B was successfully achieved to verify the hypothetical biosynthesis of phaeosphaeride B from phaeosphaeride A.</p><p>This article reviews the total synthesis and biological evaluations of phaeosphaerides A and B, and related molecules. Also, synthetic studies toward related natural products, including paraphaeosphaeride C, and structure-activity relationship studies of phaeosphaeride derivatives are discussed.</p>
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 80 (8), 755-765, 2022-08-01
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390011540582264960
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 032334471
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- KAKEN
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- Abstract License Flag
- Disallowed