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可见光促进的环状叔胺 C-H 氧化反应:具有抗病毒活性的合成士的宁生物碱的获得途径。

Visible-Light-Driven C-H Oxidation of Cyclic Tertiary Amines: Access to Synthetic Strychnos Alkaloids with Antiviral Activity.

机构信息

Organic Chemistry Chair I and Interdisciplinary Center for, Molecular Materials (ICMM), Friedrich-Alexander University of Erlangen-Nürnberg, Nikolaus-Fiebiger-Strasse 10, 91058 Erlangen, Germany.

Institute for Clinical and Molecular Virology, Friedrich-Alexander University of Erlangen-Nürnberg, Schlossgarten 4, 91054, Erlangen, Germany.

出版信息

Chemistry. 2019 Mar 15;25(16):4062-4066. doi: 10.1002/chem.201900078. Epub 2019 Mar 1.

DOI:10.1002/chem.201900078
PMID:30620121
Abstract

Air and visible light have been used in facile direct C-H oxidation of cyclic tertiary amines at ambient conditions, employing organic dyes as photocatalysts and LED. Tolerance of this new environmentally compatible protocol to various side-chain derivatizations of tryptoline and tetrahydroisoquinoline substrates was demonstrated. The developed method provides a straightforward and sustainable route towards δ-lactams, which feature strong antiviral properties (EC down to 4.6±1.8 μm) against human cytomegalovirus (HCMV). The clear advantages, which are easily available and inexpensive reagents, organic dyes, visible light, air/O and atom efficiency, make this system highly appealing for synthesis of versatile Strychnocarpine alkaloid derivatives with antiviral activity.

摘要

空气和可见光在环境条件下被用于简单直接的环状叔胺 C-H 氧化,采用有机染料作为光催化剂和 LED。该新的环境兼容方法对色胺和四氢异喹啉底物的各种侧链衍生化具有耐受性。所开发的方法为 δ-内酰胺提供了一种直接且可持续的途径,这些内酰胺具有针对人巨细胞病毒(HCMV)的强抗病毒特性(EC 低至 4.6±1.8μm)。该体系具有明显的优势,如易于获得且廉价的试剂、有机染料、可见光、空气/O 和原子效率,使其非常适合合成具有抗病毒活性的多功能士的宁生物碱衍生物。

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