title: Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.
abstract: Several C-1 homologues of pancratistatin and 7-deoxypancratistatin were synthesized by a phenanthrene-phenathridone oxidative recyclization strategy. The key steps involved the enzymatic dihydroxylation of bromobenzene, addition of an aryl alane to an epoxyaziridine, an intramolecular aziridine opening on silica gel in solid phase, and the above-mentioned recylization strategy. Experimental and spectral data are reported for all new compounds. All synthesized C-1 homologues of pancratistatin and 7-deoxypancratistatin were evaluated for antiproliferative activity in a panel of human cancer cell lines. As expected, the 7-hydroxy compounds were found to be more potent and the activity of the C-1 benzoxymethyl analogue exceeded that of narciclasine, which was used as a positive control.
authors.affiliation: Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, ON L2S 3A1, Canada.
authors.forename: Sergey
authors.initials: S
authors.lastname: Vshyvenko
authors.affiliation: Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, ON L2S 3A1, Canada.
authors.forename: Jon
authors.initials: J
authors.lastname: Scattolon
authors.affiliation: Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, ON L2S 3A1, Canada.
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
authors.affiliation: Chemistry Department, New Mexico Institute of Mining and Technology, 801 Leroy Place, Socorro, NM 87801, USA.
authors.forename: Anntherese E
authors.initials: AE
authors.lastname: Romero
authors.affiliation: Chemistry Department, New Mexico Institute of Mining and Technology, 801 Leroy Place, Socorro, NM 87801, USA.
authors.forename: Alexander
authors.initials: A
authors.lastname: Kornienko
authors.affiliation: Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, ON N9B 3P4, Canada.
authors.forename: Dennis
authors.initials: D
authors.lastname: Ma
authors.affiliation: Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, ON N9B 3P4, Canada.
authors.forename: Ian
authors.initials: I
authors.lastname: Tuffley
authors.affiliation: Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, ON N9B 3P4, Canada.
authors.forename: Siyaram
authors.initials: S
authors.lastname: Pandey
keywords: C-1 homologues of pancratistatin; amaryllidaceae alkaloids; anticancer activities; intramolecular aziridine opening; solid-phase silica catalysis