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J Am Chem Soc. 2008 Jul 30;130(30):10019-23. doi: 10.1021/ja802803e. Epub 2008 Jul 4.

Chemical synthesis and biological evaluation of palmerolide A analogues.

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1
Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences(ICES), Agency for Science, Technology and Research (A*STAR), Singapore. kcn@scripps.edu

Abstract

Molecular design and chemical synthesis of several palmerolide A analogues allowed the first structure activity relationships (SARs) of this newly discovered marine antitumor agent. From several analogues synthesized and tested (ent- 1, 5- 14, 21- 26, 50, 51), compounds 25 (with a phenyl substituent on the side chain) and 51 (lacking the C-7 hydroxyl group) were the most interesting, exhibiting approximately a 10-fold increase in potency and equipotency, respectively, to the natural product. These findings point the way to more focused structure activity relationship studies.

PMID:
18598030
DOI:
10.1021/ja802803e
[Indexed for MEDLINE]
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