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Communication

Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents

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
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Academic Editors: Ana Maria Gomez Neo and Carlos Fernández Marcos
Molecules 2021, 26(6), 1654; https://doi.org/10.3390/molecules26061654
Received: 25 February 2021 / Revised: 12 March 2021 / Accepted: 14 March 2021 / Published: 16 March 2021
(This article belongs to the Special Issue New Approach in Multicomponent Reactions)
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). View Full-Text
Keywords: multicomponent synthesis; Ugi reaction; α-aminophosphonates; tetrasubstituted carbons; antiproliferative effect multicomponent synthesis; Ugi reaction; α-aminophosphonates; tetrasubstituted carbons; antiproliferative effect
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MDPI and ACS Style

López-Francés, A.; del Corte, X.; Martínez de Marigorta, E.; Palacios, F.; Vicario, J. Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents. Molecules 2021, 26, 1654. https://doi.org/10.3390/molecules26061654

AMA Style

López-Francés A, del Corte X, Martínez de Marigorta E, Palacios F, Vicario J. Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents. Molecules. 2021; 26(6):1654. https://doi.org/10.3390/molecules26061654

Chicago/Turabian Style

López-Francés, Adrián, Xabier del Corte, Edorta Martínez de Marigorta, Francisco Palacios, and Javier Vicario. 2021. "Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents" Molecules 26, no. 6: 1654. https://doi.org/10.3390/molecules26061654

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