Synthesis of Tetrasubstituted Phosphorus Analogs of Aspartic Acid as Antiproliferative Agents
| Autor: | F Palacios, Xabier Del Corte Solaguren-Beascoa, Javier Vicario, Aitor Maestro, Adrián López-Francés |
|---|---|
| Rok vydání: | 2022 |
| Předmět: |
Aspartic Acid
Organic Chemistry Organophosphonates Pharmaceutical Science Phosphorus Antineoplastic Agents Reformatsky reaction tetrasubstituted α-aminophosphonates aspartic acid antiproliferative effect Analytical Chemistry Chemistry (miscellaneous) Cell Line Tumor Drug Discovery Humans Molecular Medicine Physical and Theoretical Chemistry |
| Zdroj: | Molecules; Volume 27; Issue 22; Pages: 8024 |
| ISSN: | 1420-3049 |
| Popis: | An efficient general method for the synthesis of a wide family of α-aminophosphonate analogs of aspartic acid bearing tetrasubstituted carbons is reported through an aza-Reformatsky reaction of α-iminophosphonates, generated from α-aminophosphonates, in an umpolung process. In addition, the α-aminophosphonate substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines A549 (carcinomic human alveolar basal epithelial cell) and SKOV3 (human ovarian carcinoma). In view of the possibilities in the diversity of the substituents that offer the synthetic methodology, an extensive profile structure–activity is presented, measuring IC50 values up to 0.34 µM in the A549 and 9.8 µM in SKOV3 cell lines. Financial support by Ministerio de Economía, Industria y Competividad (PID2021-122558OB-I00) and Gobierno Vasco (GV-IT1701-22) is gratefully acknowledged. X.d.C. and A.L.-F. thank the Basque Country Government for a predoctoral grant. |
| Databáze: | OpenAIRE |
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