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Abstract <p>This study describes synthesis and biological evaluation of a new phosphonamidate and a series of α-aminophosphonates, employing propargylamine as a key NH-nucleophilic synthon. Two synthetic approaches were successfully implemented: (i) the reaction with <i>O</i>-ethyl (3,5-di-<i>tert</i>-butyl-4-hydroxybenzyl)phosphonоchloridate to form a P–N bond; (ii) a 1,6-aza-Michael addition to dialkyl/diphenyl [(3,5-di-<i>tert</i>-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate, affording the α-aminophosphonate scaffold via C–N bond formation. Initial in vitro cytotoxicity screening against a panel of human cancer cell lines using the MTT assay revealed that the phosphonamidate derivative exhibited the highest activity within the synthesized series.</p>

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Synthesis and Cytotoxicity Evaluation of Novel Phosphonamidate and Aminophosphonates Containing Sterically Hindered Phenol and Terminal Propargyl Fragments

  • 期刊论文

  • 发表日期：

    2025年10月31日

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  • Elmira M. Gibadullina,
  • Hoang Bao Tran Nguyen,
  • Adel M. Shakirov,
  • Kseniya A. Kozyulina,
  • Anna G. Strelnik,
  • Anna P. Lyubina,
  • Aleksandra D. Voloshina,
  • Aleksandr R. Burilov,
  • Igor V. Alabugin

摘要

Abstract

This study describes synthesis and biological evaluation of a new phosphonamidate and a series of α-aminophosphonates, employing propargylamine as a key NH-nucleophilic synthon. Two synthetic approaches were successfully implemented: (i) the reaction with O-ethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonоchloridate to form a P–N bond; (ii) a 1,6-aza-Michael addition to dialkyl/diphenyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate, affording the α-aminophosphonate scaffold via C–N bond formation. Initial in vitro cytotoxicity screening against a panel of human cancer cell lines using the MTT assay revealed that the phosphonamidate derivative exhibited the highest activity within the synthesized series.