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.

中文翻译：

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作为 CREB ​​介导的基因转录抑制前药的 O-氨基萘酚 AS-E 的合成和评价

O-胺化萘酚 AS-E 被设计为前药，以实现还原活化和改善水溶性。在这种设计的化合物的合成过程中，发现了从芳基三氟甲磺酸酯和乙酰羟肟酸乙酯到恶唑的新转化。虽然最初设计的 O-氨基萘酚 AS-E 没有成功制备，但最终合成的 O-叔丁基氨基衍生物被发现具有生物活性，表明由于不利的空间和电子效应，该化合物中的还原性 NO 裂解并不容易.