Synthesis of the Biologically Active Natural Product Cyclodepsipeptides Apratoxin A and Its Analogues
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- Doi Takayuki
- Graduate School of Pharmaceutical Sciences, Tohoku University
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Abstract
This paper describes the synthetic studies conducted on a marine natural product, cyclodepsipeptide apratoxin A. Total synthesis of the oxazoline analogue of apratoxin A was achieved. The conversion of oxazoline to thioamide, as well as thioamide formation from a serine-derived compound, were both unsuccessful. However, thiazoline formation from a cysteine-derived compound led to the total synthesis of apratoxin A. An in vivo study on synthetic apratoxin A revealed that it has potent antitumor activity, but with significant toxicity. Solid-phase synthesis of apratoxin A was accomplished using a preformed thiazoline derivative as a coupling unit. This method was used to synthesize several azido-containing analogues as precursors of molecular probes, and these analogues exhibited potent biological activity.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 62 (8), 735-743, 2014
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001204177576576
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- NII Article ID
- 130004677390
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- NII Book ID
- AA00602100
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- COI
- 1:STN:280:DC%2BC2cbos1CrsQ%3D%3D
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 025609771
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- PubMed
- 25087625
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed