title: Total synthesis of isoprekinamycin: structural evidence for enhanced diazonium ion character and growth inhibitory activity toward cancer cells.
abstract: The structurally novel diazobenzo[a]fluorene antibiotic isoprekinamycin (IPK) has been synthesized for the first time employing a Suzuki coupling of a brominated AB ring synthon with a boronate ester representing the D ring, followed by anionic cyclization and appropriate functional group manipulations. The first indication that the diazobenzo[a]fluorene system exhibits in vitro anticancer activity is provided and X-ray crystallographic evidence for enhancement of diazonium ion character as a consequence of intramolecular H-bonding is described.
authors.affiliation: Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada.
authors.forename: Wei
authors.initials: W
authors.lastname: Liu
authors.forename: Matthew
authors.initials: M
authors.lastname: Buck
authors.forename: Nan
authors.initials: N
authors.lastname: Chen
authors.forename: Muhong
authors.initials: M
authors.lastname: Shang
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Taylor
authors.forename: Jalil
authors.initials: J
authors.lastname: Asoud
authors.forename: Xing
authors.initials: X
authors.lastname: Wu
authors.forename: Brian B
authors.initials: BB
authors.lastname: Hasinoff
authors.forename: Gary I
authors.initials: GI
authors.lastname: Dmitrienko
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D006860:Hydrogen Bonding; D015394:Molecular Structure
chemical_list: D000970:Antineoplastic Agents; D003979:Diazonium Compounds; D005449:Fluorenes; C523171:isoprekinamycin