title: Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties.
abstract: The 2,4'- and 4,4'-linked variants of the cytotoxic agent secalonic acid A and their analogues have been synthesized. Kinetic resolution of an unprotected tetrahydroxanthone scaffold followed by copper-mediated biaryl coupling allowed for efficient access to these compounds. Evaluation of the "shapeshifting" properties of 2,2'-, 2,4'-, and 4,4'-linked variants of the secalonic acids A in a polar solvent in conjunction with assays of the compounds against select cancer cell lines was conducted to study possible correlations between linkage variation and cytotoxicity.
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors.forename: Tian
authors.initials: T
authors.lastname: Qin
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Iwata
authors.affiliation: Molecular Targets Laboratory, Frederick National Laboratory for Cancer Research, National Cancer Institute , Frederick, Maryland 21702, United States.
authors.forename: Tanya T
authors.initials: TT
authors.lastname: Ransom
authors.affiliation: Molecular Targets Laboratory, Frederick National Laboratory for Cancer Research, National Cancer Institute , Frederick, Maryland 21702, United States.
authors.forename: John A
authors.initials: JA
authors.lastname: Beutler
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D045744:Cell Line, Tumor; D019281:Dimerization; D006801:Humans; D007700:Kinetics; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D044004:Xanthones