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

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...

Descripción completa

Detalles Bibliográficos
Autores principales: López-Francés, Adrián, del Corte, Xabier, Martínez de Marigorta, Edorta, Palacios, Francisco, Vicario, Javier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8002371/
https://www.ncbi.nlm.nih.gov/pubmed/33809715
http://dx.doi.org/10.3390/molecules26061654
_version_ 1783671448031723520
author López-Francés, Adrián
del Corte, Xabier
Martínez de Marigorta, Edorta
Palacios, Francisco
Vicario, Javier
author_facet López-Francés, Adrián
del Corte, Xabier
Martínez de Marigorta, Edorta
Palacios, Francisco
Vicario, Javier
author_sort López-Francés, Adrián
collection PubMed
description 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).
format Online
Article
Text
id pubmed-8002371
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-80023712021-03-28 Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents López-Francés, Adrián del Corte, Xabier Martínez de Marigorta, Edorta Palacios, Francisco Vicario, Javier Molecules Communication 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). MDPI 2021-03-16 /pmc/articles/PMC8002371/ /pubmed/33809715 http://dx.doi.org/10.3390/molecules26061654 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
López-Francés, Adrián
del Corte, Xabier
Martínez de Marigorta, Edorta
Palacios, Francisco
Vicario, Javier
Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
title Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
title_full Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
title_fullStr Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
title_full_unstemmed Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
title_short Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents
title_sort ugi reaction on α-phosphorated ketimines for the synthesis of tetrasubstituted α-aminophosphonates and their applications as antiproliferative agents
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8002371/
https://www.ncbi.nlm.nih.gov/pubmed/33809715
http://dx.doi.org/10.3390/molecules26061654
work_keys_str_mv AT lopezfrancesadrian ugireactiononaphosphoratedketiminesforthesynthesisoftetrasubstitutedaaminophosphonatesandtheirapplicationsasantiproliferativeagents
AT delcortexabier ugireactiononaphosphoratedketiminesforthesynthesisoftetrasubstitutedaaminophosphonatesandtheirapplicationsasantiproliferativeagents
AT martinezdemarigortaedorta ugireactiononaphosphoratedketiminesforthesynthesisoftetrasubstitutedaaminophosphonatesandtheirapplicationsasantiproliferativeagents
AT palaciosfrancisco ugireactiononaphosphoratedketiminesforthesynthesisoftetrasubstitutedaaminophosphonatesandtheirapplicationsasantiproliferativeagents
AT vicariojavier ugireactiononaphosphoratedketiminesforthesynthesisoftetrasubstitutedaaminophosphonatesandtheirapplicationsasantiproliferativeagents

Ejemplares similares