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 <i>N</i>-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 elimi...
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/6/1654 |
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| author | Adrián López-Francés Xabier del Corte Edorta Martínez de Marigorta Francisco Palacios Javier Vicario |
| author_facet | Adrián López-Francés Xabier del Corte Edorta Martínez de Marigorta Francisco Palacios Javier Vicario |
| author_sort | Adrián López-Francés |
| collection | DOAJ |
| description | An Ugi three-component reaction using preformed α-phosphorated <i>N</i>-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). |
| first_indexed | 2024-03-10T13:11:56Z |
| format | Article |
| id | doaj.art-bd83ba60f2774eb98ef377f29aa8c933 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T13:11:56Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-bd83ba60f2774eb98ef377f29aa8c9332023-11-21T10:45:00ZengMDPI AGMolecules1420-30492021-03-01266165410.3390/molecules26061654Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative AgentsAdrián López-Francés0Xabier del Corte1Edorta Martínez de Marigorta2Francisco Palacios3Javier Vicario4Departamento 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, SpainDepartamento 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, SpainDepartamento 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, SpainDepartamento 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, SpainDepartamento 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, SpainAn Ugi three-component reaction using preformed α-phosphorated <i>N</i>-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).https://www.mdpi.com/1420-3049/26/6/1654multicomponent synthesisUgi reactionα-aminophosphonatestetrasubstituted carbonsantiproliferative effect |
| spellingShingle | Adrián López-Francés Xabier del Corte Edorta Martínez de Marigorta Francisco Palacios Javier Vicario Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents Molecules multicomponent synthesis Ugi reaction α-aminophosphonates tetrasubstituted carbons antiproliferative effect |
| 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 | multicomponent synthesis Ugi reaction α-aminophosphonates tetrasubstituted carbons antiproliferative effect |
| url | https://www.mdpi.com/1420-3049/26/6/1654 |
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