2. Academic Validation
  3. Synthesis and Evaluation of an O-Aminated Naphthol AS-E as a Prodrug of CREB-mediated Gene Transcription Inhibition

Synthesis and Evaluation of an O-Aminated Naphthol AS-E as a Prodrug of CREB-mediated Gene Transcription Inhibition

  • Lett Org Chem. 2013 Jun;10(5):380-384. doi: 10.2174/1570178611310050014.
Fuchun Xie 1,  Bingbing X Li 1,  Xiangshu Xiao 2
Affiliations

Affiliations

  • 1 Program in Chemical Biology, Department of Physiology and Pharmacology, Oregon Health & Science University, Portland, OR 97239, USA.
  • 2 Program in Chemical Biology, Department of Physiology and Pharmacology, Oregon Health & Science University, Portland, OR 97239, USA ; Knight Cancer Institute, Oregon Health & Science University, Portland, OR 97239, USA.
PMID: 25285062 DOI: 10.2174/1570178611310050014
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.

Keywords

CREB; O-amination; ethyl acetohydroximate; naphthol AS-E; oxazole; prodrug; reductive activation.

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