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Synthesis and Anti-Proliferative Activity of New α-Amino Phosphonate Derivatives Bearing Heterocyclic Moiety

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Pharmaceutical Chemistry Journal Aims and scope

Condensation of 4-chloroacetophenone 1 with phenyl hydrazine 2 afforded hydrazone 3. Further reaction of 3 with Vilsmeier reagent yielded the pyrazolaldehyde 4 in excellent yield. A one-pot, three-component reaction between aldehyde 4, triphenylphosphite 5, and appropriate amines in the presence of lithium perchlorate as Lewis acid catalyst gave the corresponding α-amino phosphonates 7-12(a-d) in good yields. The chemical structures of all new compounds were established by IR, 1H NMR, and mass spectroscopy analysis. The anti-proliferative activity of the synthesized compounds against HCT-116, HepG2 and MCF-7 human cancer cells using the MTT assay was evaluated, and revealed higher anticancer activity when compared with reference drug doxorubicin. Among the tested compounds, pyrazole derivatives 4 and 9 exhibited the highest anticancer activity against breast (MCF-7), and colon (HCT-116) cancer cell lines with IC50 = 2.7 and 3.3 μM, respectively.

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Acknowledgments

We would like to acknowledge financial support of the Menoufia University throughout project No Ib-2013.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt

    Ramzy E. Abdelwahed, Ahmed A. El Gokha & Ibrahim El-Tantawy El Sayed

  2. Nursing Department, Al-Suwaria Technical Institute, Middle Technical University, Baghdad, Iraq

    Ahmed Habeeb Radhi

  3. Department of Tanning Materials and Leather Technology, National Research Centre, Dokki, Giza, Egypt

    Hanem M. Awad

  4. Tanta Higher Institute of Engineering and Technology, Tanta, Egypt

    Adel E-S. Goda

Authors
  1. Ramzy E. Abdelwahed
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  2. Ahmed Habeeb Radhi
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  3. Hanem M. Awad
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  4. Ahmed A. El Gokha
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  5. Adel E-S. Goda
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  6. Ibrahim El-Tantawy El Sayed
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Correspondence to Ibrahim El-Tantawy El Sayed.

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Abdelwahed, R.E., Radhi, A.H., Awad, H.M. et al. Synthesis and Anti-Proliferative Activity of New α-Amino Phosphonate Derivatives Bearing Heterocyclic Moiety. Pharm Chem J 55, 231–239 (2021). https://doi.org/10.1007/s11094-021-02404-1

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  • DOI: https://doi.org/10.1007/s11094-021-02404-1

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