Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
Adrián López‐Francés, Xabier del Corte, Edorta Martínez de Marigorta, Francisco Palácios, Javier Vicario
Abstract
-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).
Topics & Concepts
Steric effectsChemistryArylCytotoxicityIn vitroCombinatorial chemistryStereochemistryOrganic chemistryBiochemistryAlkylMulticomponent Synthesis of HeterocyclesPhosphorus compounds and reactionsClick Chemistry and Applications