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2-氧代吲哚及相关杂环化合物:其天然产物及相关衍生物的合成方法

2-Oxindole and related heterocycles: synthetic methodologies for their natural products and related derivatives.

作者信息

Sharma Shivangi, Monga Yukti, Gupta Ashu, Singh Shivendra

机构信息

Department of Applied Chemistry, Amity School of Engineering and Technology, Amity University Madhya Pradesh Gwalior Madhya Pradesh-474 005 India

Shyamlal College, Department of Chemistry, University of Delhi Delhi-110032 India.

出版信息

RSC Adv. 2023 May 11;13(21):14249-14267. doi: 10.1039/d3ra02217j. eCollection 2023 May 9.

Abstract

Natural goods, medications, and pharmaceutically active substances all contain substituted oxindoles. Generally, the C-3 stereocenter of the substituents of oxindoles and their absolute arrangement have a substantial impact on the bioactivity of these substances. In this case, the desire for contemporary probe and drug-discovery programs for the synthesis of chiral compounds using desirable scaffolds with high structural diversity further drives research in this field. Also, the new synthetic techniques are generally simple to apply for the synthesis of other similar scaffolds. Herein, we review the distinct approaches for the synthesis of diverse useful oxindole scaffolds. Specifically, the research findings on the naturally existing 2-oxindole core and a variety of synthetic compounds having a 2-oxindole core are discussed. We present an overview of the construction of oxindole-based synthetic and natural products. In addition, the chemical reactivity of 2-oxindole and its related derivatives in the presence of chiral and achiral catalysts are thoroughly discussed. The data compiled herein provides broad information related to the bioactive product design, development, and applications of 2-oxindoles and the reported techniques will be helpful for the investigation of novel reactions in the future.

摘要

天然产物、药物和具有药理活性的物质中均含有取代吲哚酮。一般来说,吲哚酮取代基的C-3立体中心及其绝对构型对这些物质的生物活性有重大影响。在这种情况下,利用具有高度结构多样性的理想骨架合成手性化合物的当代探针和药物发现计划的需求,进一步推动了该领域的研究。此外,新的合成技术通常易于应用于其他类似骨架的合成。在此,我们综述了合成各种有用的吲哚酮骨架的不同方法。具体讨论了天然存在的2-吲哚酮核心以及具有2-吲哚酮核心的各种合成化合物相关的研究结果。我们概述了基于吲哚酮的合成产物和天然产物的构建。此外,还深入讨论了2-吲哚酮及其相关衍生物在手性和非手性催化剂存在下的化学反应性。本文汇编的数据提供了与2-吲哚酮生物活性产物设计、开发和应用相关的广泛信息,所报道的技术将有助于未来新型反应的研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c95a/10173257/0701d42b7e03/d3ra02217j-f1.jpg

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