Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents |
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| Authors: | Adrin Lpez-Francs Xabier del Corte Edorta Martínez de Marigorta Francisco Palacios Javier Vicario |
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| Institution: | 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; (A.L.-F.); (X.d.C.); (E.M.d.M.) |
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| Abstract: | An Ugi three-component reaction using preformed α-phosphorated N-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). |
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| Keywords: | multicomponent synthesis Ugi reaction α -aminophosphonates tetrasubstituted carbons antiproliferative effect |
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