Strecker reaction and α-amino nitriles: Recent advances in their chemistry, synthesis, and biological properties

化学 氰化 Strecker胺基酸合成 部分 组合化学 农药 生物活性 化学合成 有机化学 药物发现 对映选择合成 催化作用 生物化学 体外 生态学 生物 农业
作者
Vladímir V. Kouznetsov,Carlos E. Puerto Galvis
出处
期刊:Tetrahedron [Elsevier BV]
卷期号:74 (8): 773-810 被引量:134
标识
DOI:10.1016/j.tet.2018.01.005
摘要

α-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 α-amino nitrile moiety has been found in the structure of different alkaloids, while the α-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 α-amino nitriles through the Strecker-type and α-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 α-aminonitrile-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 α-amidoacetonitrile derivatives as potent and selective protease inhibitors as well as promising pesticidal agents were briefly reviewed. The bibliography includes 461 references.
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