Faculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran.
Institut Für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, 40204, Düsseldorf, Germany.
Amino Acids. 2021 Jan;53(1):1-10. doi: 10.1007/s00726-020-02917-1. Epub 2020 Nov 27.
Isocyanide-based consecutive Bargellini/Ugi multicomponent reactions as a combinatorial strategy have been developed for the synthesis of new class of pseudo-peptides. Via Bargellini reaction 3-carboxamido-isobutyric acids are prepared using acetone, chloroform, sodium hydroxide, and isocyanides. Then, using Ugi multicomponent reaction strategy, pseudo-peptides containing three amide bonds are synthesized using the Bargellini reaction product, aldehydes, amines, and isocyanides. This is an efficient and eco-friendly approach for easy access to wide variety of structurally diverse, drug-like pseudo-peptides from cheap and readily available precursors in high yields.
基于异氰化物的连续 Bargellini/Ugi 多组分反应已被开发用于合成新型伪肽。通过 Bargellini 反应,使用丙酮、氯仿、氢氧化钠和异氰化物制备 3-羧酰胺基异丁酸。然后,使用 Ugi 多组分反应策略,使用 Bargellini 反应产物、醛、胺和异氰化物合成含有三个酰胺键的伪肽。这是一种高效、环保的方法,可从廉价且易得的前体中以高产率轻松获得广泛的结构多样的类药性伪肽。