通过与水兼容的金催化加氢反应合成菲啶衍生物

IF 4.3 3区 材料科学 Q1 ENGINEERING, ELECTRICAL & ELECTRONIC ACS Applied Electronic Materials Pub Date : 2024-09-16 DOI:10.1016/j.bmc.2024.117928
Yixuan Lin , Riichi Hashimoto , Tsung-Che Chang , Katsunori Tanaka
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引用次数: 0

摘要

由于过渡金属催化反应是合成有机分子最强大、最直接的方法之一,因此将其转化到生物系统中进行生物医学应用是一个新兴领域。在生物环境中操纵过渡金属反应以释放原药和合成具有生物活性的药物已被广泛研究。为了扩展过渡金属介导的原药策略工具箱,本研究介绍了 2′-炔基联苯胺前体,在温和条件下利用水相容性金催化加氢合成菲啶衍生物。此外,结构-反应关系显示,前体中胺基的亲核性是促进金催化合成菲啶衍生物的关键。这项研究显示了在水溶液中设计基于菲啶的原药的潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Synthesis of phenanthridine derivatives by a water-compatible gold-catalyzed hydroamination

Since transition-metal-catalyzed reactions are one of the most powerful and direct approaches for the synthesis of organic molecules, translating them to biological systems for biomedical applications is an emerging field. The manipulation of transition metal reactions in biological settings for uncaging prodrugs and synthesizing bioactive drugs has been widely studied. To expand the toolbox of transition-metal-mediated prodrug strategy, this work introduces the 2′-alkynl-biphenylamine precursors for the synthesis of phenanthridine derivatives using a water-compatible gold-catalyzed hydroamination under mild conditions. Moreover, the structure–reactivity relationship revealed that the nucleophilicity of the amine group in the precursor was critical for facilitating the gold-catalyzed synthesis of phenanthridine derivatives. The research shows the potential to be used for phenanthridine-based prodrug designs in an aqueous solution.

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7.20
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4.30%
发文量
567
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