title: Synthesis and Evaluation of anO-Aminated Naphthol AS-E as a Prodrug of CREB-mediated Gene Transcription Inhibition.
abstract: AnO-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 designedO-amino naphthol AS-E was not made successfully, the eventually synthesizedO-tert-butylamino derivative was found to be biologically inactive, suggesting that reductiveN-Ocleavage in this compound was not facile due to unfavorable steric and electronic effects.
authors.affiliation: Program in Chemical Biology, Department of Physiology and Pharmacology, Oregon Health & Science University, Portland, OR 97239, USA.
authors.forename: Fuchun
authors.initials: F
authors.lastname: Xie
authors.affiliation: Program in Chemical Biology, Department of Physiology and Pharmacology, Oregon Health & Science University, Portland, OR 97239, USA.
authors.forename: Bingbing X
authors.initials: BX
authors.lastname: Li
authors.affiliation: 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.
authors.forename: Xiangshu
authors.initials: X
authors.lastname: Xiao
keywords: CREB; O-amination; ethyl acetohydroximate; naphthol AS-E; oxazole; prodrug; reductive activation