AI Article Synopsis
- The study focuses on modifying the natural product griseofulvin to enhance its solubility and stability in metabolism.
- Two main strategies were employed: converting aryl methyl ethers to aryl difluoromethyl ethers at key metabolic sites, and altering the C-ring ketone into polar oximes.
- The research finds that the polar oxime formation is the most effective approach for improving the characteristics of the modified griseofulvin analogues.
Article Abstract
We report two types of modifications to the natural product griseofulvin as strategies to improve solubility and metabolic stability: the conversion of aryl methyl ethers into aryl difluoromethyl ethers at metabolic hotspots and the conversion of the C-ring ketone into polar oximes. The syntheses of the analogues are described together with their solubility, metabolic half-life in vitro and antiproliferative effect in two cancer cell lines. We conclude that on balance, the formation of polar oximes is the most promising strategy for improving the properties of the analogues.
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| http://dx.doi.org/10.1016/j.ejmech.2016.03.071 | DOI Listing |
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