Document Detail

Synthesis of phidianidines A and B.
MedLine Citation:
PMID:  22524523     Owner:  NLM     Status:  MEDLINE    
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.
Hong-Yu Lin; Barry B Snider
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-05-01
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  77     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 May 
Date Detail:
Created Date:  2012-05-18     Completed Date:  2012-09-10     Revised Date:  2013-06-25    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4832-6     Citation Subset:  IM    
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, United States.
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MeSH Terms
Indole Alkaloids / chemical synthesis*,  chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Oxadiazoles / chemical synthesis*,  chemistry*
Grant Support
Reg. No./Substance:
0/Indole Alkaloids; 0/Oxadiazoles; 0/phidianidine A; 0/phidianidine B

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