TY - JOUR
T1 - Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages
T2 - Investigation of "shapeshifting" Properties
AU - Qin, Tian
AU - Iwata, Takayuki
AU - Ransom, Tanya T.
AU - Beutler, John A.
AU - Porco, John A.
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/12/9
Y1 - 2015/12/9
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.5b09825
DO - 10.1021/jacs.5b09825
M3 - Article
C2 - 26544765
AN - SCOPUS:84949575626
SN - 0002-7863
VL - 137
SP - 15225
EP - 15233
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 48
ER -