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<p>New derivatives of oleanane triterpenoids containing a <i>gem</i>-nitrochloro-substituted quaternary carbon atom in ring A were synthesized from betulin and oleanolic acid by a sequence of simple chemical reactions. The key stage of the transformations was the oxidative chlorination of triterpenoid oximes with Oxone® in the presence of sodium chloride in an aqueous-organic medium. Analysis of cytotoxicity of new compounds revealed the hormesis effect. The nitrochloro derivatives of oleanane triterpenoids in the nanomolar concentration range enhance the proliferation of human embryonic kidney cells Hek293, while at micromolar concentrations they reduce their viability.</p>

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Synthesis and evaluation of cytotoxic activity of new gem-nitrochloro-substituted oleanane triterpenoids

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • E. Yu. Yamansarov,
  • O. B. Kazakova,
  • A. N. Lobov,
  • K. V. Danilko,
  • V. A. Solntzev,
  • R. V. Plotnitskii,
  • E. I. Seleznev,
  • E. K. Beloglazkina

摘要

New derivatives of oleanane triterpenoids containing a gem-nitrochloro-substituted quaternary carbon atom in ring A were synthesized from betulin and oleanolic acid by a sequence of simple chemical reactions. The key stage of the transformations was the oxidative chlorination of triterpenoid oximes with Oxone® in the presence of sodium chloride in an aqueous-organic medium. Analysis of cytotoxicity of new compounds revealed the hormesis effect. The nitrochloro derivatives of oleanane triterpenoids in the nanomolar concentration range enhance the proliferation of human embryonic kidney cells Hek293, while at micromolar concentrations they reduce their viability.