title: Synthesis of phidianidines A and B.
abstract: 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.
authors.affiliation: Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, United States.
authors.forename: Hong-Yu
authors.initials: HY
authors.lastname: Lin
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; D010069:Oxadiazoles; C559224:phidianidine A; C559225:phidianidine B