| Synthesis of Phidianidines A and B. | |
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MedLine Citation:
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PMID: 22524523 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl¬-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)-methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10-5 M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A. |
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Authors:
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Hong-Yu Lin; Barry B Snider |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-4-23 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2012 Apr |
Date Detail:
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Created Date: 2012-4-24 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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