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Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of “Shapeshifting” Properties

2015; American Chemical Society; Volume: 137; Issue: 48 Linguagem: Inglês

10.1021/jacs.5b09825

1943-2984

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

Marine Sponges and Natural Products

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.