Synthesis and evaluation of an O-Aminated naphthol AS-E as a prodrug of CREB-mediated gene transcription inhibition

Fuchun Xie, Bingbing X. Li, Xiangshu Xiao

Research output: Contribution to journalArticle

4 Scopus citations

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 languageEnglish (US)
Pages (from-to)380-384
Number of pages5
JournalLetters in Organic Chemistry
Volume10
Issue number5
DOIs
StatePublished - Jun 1 2013

Keywords

  • CREB
  • Ethyl acetohydroximate
  • Naphthol AS-E
  • O-Amination
  • Oxazole
  • Prodrug
  • Reductive activation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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