title: Synthesis and evaluation of a novel E-ring modified alpha-hydroxy keto ether analogue of camptothecin.
abstract: The synthesis of a novel E-ring modified keto ether analogue of camptothecin and homocamptothecin by the cascade radical annulation route is reported. The analogue, Du1441, is an isomer of homocamptothecin, but includes the alpha-hydroxy carbonyl functionality that camptothecin possesses and homocamptothecin lacks. Despite these similarities, the new keto ether analogue is inactive in cell assays, and implications for the structure/activity relationship are discussed.
authors.affiliation: University of Pittsburgh, Department of Chemistry, Pittsburgh, PA 15260, USA.
authors.forename: Wu
authors.initials: W
authors.lastname: Du
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
authors.forename: Robert L
authors.initials: RL
authors.lastname: Bevins
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Zimmer
authors.forename: Junhong
authors.initials: J
authors.lastname: Zhang
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Burke
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D002166:Camptothecin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004987:Ethers / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D013057:Spectrum Analysis; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004987:Ethers; D002166:Camptothecin