Strecker reaction and α-amino nitriles: Recent advances in their chemistry, synthesis, and biological properties
Strecker reaction and α-amino nitriles: Recent advances in their chemistry, synthesis, and biological properties
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DOI：
10.1016/j.tet.2018.01.005
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发表时间：
2018-02-22
期刊：
影响因子：
2.1
通讯作者：
Puerto Galvis, Carlos E.
中科院分区：
文献类型：
--
作者：
Kouznetsov, Vladimir V.;Puerto Galvis, Carlos E.
α-氨基腈化合物对生物化学科学具有深远的影响，因为它们是由廉价的起始原料制备的，并且已成为极其重要的杂环和碳环分子的化学合成中有价值的中间体，这些分子在药理学和生物学研究中充当合适的模型。 α-氨基腈部分已在不同生物碱的结构中被发现，而α-酰胺基乙腈基团是新型抗高血糖药物和有前途的药理学和农业化学制剂的重要片段。由于它们的合成、生物学和实际重要性，本文重点介绍了通过 Strecker 型和 α-氰化反应制备 α-氨基腈的最新信息、它们的化学和生物学性质以及它们的合成应用，重点关注其为药理学、生物学和农业化学研究产生新分子多样性的出色能力，最终实现了复合物的全合成 生物碱、新型N-杂环化合物和含α-氨基腈药物的制备。分析了基于交叉脱氢偶联（CDD）工艺的Strecker型反应和氰化反应的现代合成方案，讨论了新型催化剂和绿色反应条件的优缺点。此外，还简要回顾了α-酰胺基乙腈衍生物作为有效和选择性蛋白酶抑制剂以及有前途的杀虫剂的显着生物学特性。参考书目包括 461 篇参考文献。 (C) 2018 Elsevier Ltd. 保留所有权利。
alpha-Amino nitrile compounds have a profound impact on bio-chemical sciences, as they have been prepared from inexpensive starting materials and have become valuable intermediates in the chemical synthesis of vitally important heterocyclic and carbocyclic molecules, which serve as suitable models in pharmacological and biological research. The alpha-amino nitrile moiety has been found in the structure of different alkaloids, while the alpha-amidoacetonitrile group is an essential fragment of new anti hyperglycemic drugs and promising pharmacological and agrochemical agents. Due to their synthetic, biological and practical importance, this review highlights the recent information about the preparation of alpha-amino nitriles through the Strecker-type and alpha-cyanation reactions, their chemical and biological properties, as well as their synthetic application, paying attention on the wonderful capacity for generating novel molecular diversity for pharmacological, biological and agrochemical researches, which ends with the total synthesis of complex alkaloids, preparation of new N-heterocycles and alpha-amino-nitrile-containing drugs. Analyzing modern synthetic protocols for the Strecker-type reactions and cyanation reactions based on cross-dehydrogenative coupling (CDD) process, the advantages and disadvantages of new catalysts and green reaction conditions are also discussed. In addition, remarkable biological properties of alpha-amidoacetonitrile derivatives as potent and selective protease inhibitors as well as promising pesticidal agents were briefly reviewed. The bibliography includes 461 references. (C) 2018 Elsevier Ltd. All rights reserved.