Synthesis of novel α-aminophosphonates under microwave irradiation, biological evaluation as antiproliferative agents and apoptosis inducers

The synthesis of two series of α-aminophosphonates was achieved by Microwave Irradiation (MW), using the one-pot Kabachnik–Fields reaction. Based on a green chemistry approach, the reactions were carried out using ethanol as the only solvent and without any catalyst, and short reaction times (20–40 ...

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Bibliographic Details
Published in:Medicinal chemistry research 2019-11, Vol.28 (11), p.2067-2078
Main Authors: Loredo-Calderón, Erika L., Velázquez-Martínez, Carlos A., Ramírez-Cabrera, Mónica A., Hernández-Fernández, Eugenio, Rivas-Galindo, Verónica M., Arredondo Espinoza, Eder, López-Cortina, Susana T.
Format: Article
Language:English
Subjects:
60 APPLIED LIFE SCIENCES
Antiproliferatives
APOPTOSIS
BENZOATES
Biochemistry
Biomedical and Life Sciences
Biomedicine
Biotechnology
Catalysts
Cell Biology
Cell death
Cell growth
CELL PROLIFERATION
ETHANOL
Irradiation
Kinases
MICROWAVE RADIATION
NEOPLASMS
Organic chemistry
Original Research
Pharmacology/Toxicology
PHOSPHONATES
Synthesis
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Summary:The synthesis of two series of α-aminophosphonates was achieved by Microwave Irradiation (MW), using the one-pot Kabachnik–Fields reaction. Based on a green chemistry approach, the reactions were carried out using ethanol as the only solvent and without any catalyst, and short reaction times (20–40 min), in variable yields. Both series were tested to determine their cell proliferation inhibition activity in MDA-MB-231, MCF-7 and MCF-10A cell lines. Ethyl 4-(((diphenoxyphosphoryl)(4-(diphenylamino)phenyl)methyl)amino) benzoate 4e and diphenyl (((4-(((S)-2-hydroxy-1-phenylethyl)carbamoyl)phenyl)amino)(4-hydroxyphenyl)methyl)phosphonate 6b , showed cell proliferation inhibition activity only in the cancer cell line MCF-7 and no effect on the normal cell line MFC-10A, both compounds caused cell death by inducing apoptosis.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-019-02436-z