Abstract
An O-Aminated naphthol AS-E was designed as a prodrug to achieve reductive activation and improved aqueous solubility. During the synthesis of this designed compound, a novel transformation from aryl triflates and ethyl acetohydroximate to oxazoles was discovered. Although the initially designed O-Amino naphthol AS-E was not made successfully, the eventually synthesized O-tert-butylamino derivative was found to be biologically inactive, suggesting that reductive N-O cleavage in this compound was not facile due to unfavorable steric and electronic effects.
Original language | English (US) |
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Pages (from-to) | 380-384 |
Number of pages | 5 |
Journal | Letters in Organic Chemistry |
Volume | 10 |
Issue number | 5 |
DOIs | |
State | Published - Jun 2013 |
Keywords
- CREB
- Ethyl acetohydroximate
- Naphthol AS-E
- O-Amination
- Oxazole
- Prodrug
- Reductive activation
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry