Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "shapeshifting" Properties

Tian Qin, Takayuki Iwata, Tanya T. Ransom, John A. Beutler, John A. Porco

Research output: Contribution to journalArticle

23 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)15225-15233
Number of pages9
JournalJournal of the American Chemical Society
Volume137
Issue number48
DOIs
StatePublished - Dec 9 2015
Externally publishedYes

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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