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

  • Erika L. Loredo-Calderón
  • Carlos A. Velázquez-Martínez
  • Mónica A. Ramírez-Cabrera
  • Eugenio Hernández-Fernández
  • Verónica M. Rivas-Galindo
  • Eder Arredondo Espinoza
  • Susana T. López-CortinaEmail author
Original Research
  • 37 Downloads

Abstract

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.

Keywords

Aminophosphonates Green synthesis Kabachnik–Fields Cell proliferation inhibition activity Apoptosis 

Notes

Acknowledgements

The authors thank the National Council for Science and Technology (CONACYT) for its financial support via Project 180854. ELLC, also thanks CONACYT for a Graduate Scholarship 229877.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2019_2436_MOESM1_ESM.docx (2.1 mb)
Supplementary Item

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Erika L. Loredo-Calderón
    • 1
  • Carlos A. Velázquez-Martínez
    • 2
  • Mónica A. Ramírez-Cabrera
    • 1
  • Eugenio Hernández-Fernández
    • 1
  • Verónica M. Rivas-Galindo
    • 3
  • Eder Arredondo Espinoza
    • 1
  • Susana T. López-Cortina
    • 1
    Email author
  1. 1.Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Laboratorio de Química Industrial y Laboratorio de Ingeniería Genética y Genómica Av. Universidad s/n, Cd. UniversitariaSan Nicolás De Los GarzaMexico
  2. 2.Faculty of Pharmacy and Pharmaceutical SciencesUniversity of AlbertaEdmontonCanada
  3. 3.Universidad Autónoma de Nuevo León, Facultad de MedicinaMonterreyMexico

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