title: Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.
abstract: The synthesis of two C-1 analogues of pancratistatin has been accomplished in 17 steps from bromobenzene. The key steps involved the enzymatic dihydroxylation, regioselective opening of epoxyaziridine 9 with the alane derived from 8, a solid-state silica-gel-catalyzed intramolecular opening of aziridine to produce phenanthrene 13 whose oxidative cleavage and recyclization provided the full skeleton of the Amaryllidaceae constituents. The new analogues 5 and 6 exhibited promising activity in several human cancer cell lines.
authors.affiliation: Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario, Canada L2S 3A1.
authors.forename: Sergey
authors.initials: S
authors.lastname: Vshyvenko
authors.forename: Jon
authors.initials: J
authors.lastname: Scattolon
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
authors.forename: Anntherese E
authors.initials: AE
authors.lastname: Romero
authors.forename: Alexander
authors.initials: A
authors.lastname: Kornienko
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001969:Bromobenzenes / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D047151:Amaryllidaceae Alkaloids; D000970:Antineoplastic Agents; D001969:Bromobenzenes; D007546:Isoquinolines; C044997:pancratistatin; C032036:bromobenzene