Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 48, Pages 15225-15233Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09825
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Funding
- NIH [GM-073855, GM-099920, GM-111625]
- NIGMS CMLD Initiative [P50 GM067041]
- Vertex Pharmaceuticals, Inc.
- Uehara Memorial Foundation
- NIH, National Cancer Institute, Center for Cancer Research
- Developmental Therapeutics Program, Division of Cancer Diagnosis and Treatment
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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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