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

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

Volume: 10 Issue: 5

Author(s): Fuchun Xie, Bingbing X. Li and Xiangshu Xiao

Affiliation:

Keywords: CREB, ethyl acetohydroximate, naphthol AS-E, oxazole, O-amination, prodrug, reductive activation.

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.

Cite this article as:

Xie Fuchun, Li Bingbing X. and Xiao Xiangshu, Synthesis and Evaluation of an O-Aminated Naphthol AS-E as a Prodrug of CREB-mediated Gene Transcription Inhibition, Letters in Organic Chemistry 2013; 10 (5) . https://dx.doi.org/10.2174/1570178611310050014