Departamento de Química Orgánica I, Centro de Investigación y Estudios Avanzados "Lucio Lascaray", Facultad de Farmacia, University of the Basque Country, UPV/EHU Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain.
Molecules. 2021 Mar 16;26(6):1654. doi: 10.3390/molecules26061654.
An Ugi three-component reaction using preformed α-phosphorated -tosyl ketimines with different isocyanides in the presence of a carboxylic acid affords tetrasubstituted α-aminophosphonates. Due to the high steric hindrance, the expected acylated amines undergo a spontaneous elimination of the acyl group. The reaction is applicable to α-aryl ketimines bearing a number of substituents and several isocyanides. In addition, the densely substituted α-aminophosphonate substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell line A549 (carcinomic human alveolar basal epithelial cell).
利用预形成的α-膦酰化 -对甲苯磺酰亚胺与不同的异氰化物在羧酸存在下的 Ugi 三组分反应，得到四取代的α-氨基膦酸酯。由于空间位阻较大，预期的酰化胺会自发消除酰基。该反应适用于带有多个取代基和几种异氰化物的α-芳基亚胺。此外，取代基密集的α-氨基膦酸酯底物表现出体外细胞毒性，抑制人肺癌细胞系 A549（人肺泡基底上皮癌细胞）的生长。
