Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation
Encouraged by the significant cytotoxic activity of simple α-aminophosphonates, a molecular library comprising phosphonoylmethyl- and phosphinoylmethyl-α-aminophosphonates, a tris derivative, and <i>N</i>-acylated species was established. The promising aminophosphonate derivatives were s...
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| Format: | Article |
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MDPI AG
2023-03-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/16/4/506 |
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| author | Petra R. Varga Rita Oláhné Szabó György Dormán Szilvia Bősze György Keglevich |
| author_facet | Petra R. Varga Rita Oláhné Szabó György Dormán Szilvia Bősze György Keglevich |
| author_sort | Petra R. Varga |
| collection | DOAJ |
| description | Encouraged by the significant cytotoxic activity of simple α-aminophosphonates, a molecular library comprising phosphonoylmethyl- and phosphinoylmethyl-α-aminophosphonates, a tris derivative, and <i>N</i>-acylated species was established. The promising aminophosphonate derivatives were subjected to a comparative structure–activity analysis. We evaluated 12 new aminophosphonate derivatives on tumor cell cultures of different tissue origins (skin, lung, breast, and prostate). Several derivatives showed pronounced, even selective cytostatic effects. According to IC<sub>50</sub> values, phosphinoylmethyl-aminophosphonate derivative <b>2e</b> elicited a significant cytostatic effect on breast adenocarcinoma cells, but it was even more effective against prostatic carcinoma cells. Based on our data, these new compounds exhibited promising antitumor activity on different tumor types, and they might represent a new group of alternative chemotherapeutic agents. |
| first_indexed | 2024-03-11T04:39:18Z |
| format | Article |
| id | doaj.art-6513d429a540431196740a05f361938c |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-11T04:39:18Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-6513d429a540431196740a05f361938c2023-11-17T20:49:54ZengMDPI AGPharmaceuticals1424-82472023-03-0116450610.3390/ph16040506Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and AcylationPetra R. Varga0Rita Oláhné Szabó1György Dormán2Szilvia Bősze3György Keglevich4Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, 1521 Budapest, HungaryELKH-ELTE Research Group of Peptide Chemistry, Eötvös Loránd Research Network (ELKH), Eötvös Loránd University (ELTE), 1117 Budapest, HungaryDepartment of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, 1521 Budapest, HungaryELKH-ELTE Research Group of Peptide Chemistry, Eötvös Loránd Research Network (ELKH), Eötvös Loránd University (ELTE), 1117 Budapest, HungaryDepartment of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, 1521 Budapest, HungaryEncouraged by the significant cytotoxic activity of simple α-aminophosphonates, a molecular library comprising phosphonoylmethyl- and phosphinoylmethyl-α-aminophosphonates, a tris derivative, and <i>N</i>-acylated species was established. The promising aminophosphonate derivatives were subjected to a comparative structure–activity analysis. We evaluated 12 new aminophosphonate derivatives on tumor cell cultures of different tissue origins (skin, lung, breast, and prostate). Several derivatives showed pronounced, even selective cytostatic effects. According to IC<sub>50</sub> values, phosphinoylmethyl-aminophosphonate derivative <b>2e</b> elicited a significant cytostatic effect on breast adenocarcinoma cells, but it was even more effective against prostatic carcinoma cells. Based on our data, these new compounds exhibited promising antitumor activity on different tumor types, and they might represent a new group of alternative chemotherapeutic agents.https://www.mdpi.com/1424-8247/16/4/506α-aminophosphonatesphosphonoylmethyl-α-aminophosphonatesphosphinoylmethyl-α-aminophosphonatescytotoxic activity |
| spellingShingle | Petra R. Varga Rita Oláhné Szabó György Dormán Szilvia Bősze György Keglevich Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation Pharmaceuticals α-aminophosphonates phosphonoylmethyl-α-aminophosphonates phosphinoylmethyl-α-aminophosphonates cytotoxic activity |
| title | Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation |
| title_full | Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation |
| title_fullStr | Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation |
| title_full_unstemmed | Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation |
| title_short | Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation |
| title_sort | cytotoxic activity of α aminophosphonic derivatives coming from the tandem kabachnik fields reaction and acylation |
| topic | α-aminophosphonates phosphonoylmethyl-α-aminophosphonates phosphinoylmethyl-α-aminophosphonates cytotoxic activity |
| url | https://www.mdpi.com/1424-8247/16/4/506 |
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