<p>New conjugates of lupane triterpenoids bound through a 1,2,3-triazole linker with gallate derivatives were prepared via Cu-catalyzed cycloaddition reactions of [3<i>β</i>,28-diacetoxy-20(29)-lupen-30-yl]azide and 3<i>β</i>-acetoxylup-20(29)-en-30-azido-28-oic acid with gallate derivatives with propargyl substituents in various positions. Conjugate <b>4</b> based on betulin with a modified gallate substituent containing a dioxolane moiety possessed potent antioxidant properties and anti-inflammatory activity (suppression of NO hyperexpression).</p>

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Synthesis and Biological Activity of Derivatives of (C-30)-Substituted Lupane Triterpenoids and Gallic Acid Bound Through a 1,2,3-Triazole Linker

  • S. A. Popov,
  • Z. Qi,
  • G. Yang,
  • C. Wang,
  • M. D. Semenova,
  • A. V. Shpatov,
  • E. E. Shults

摘要

New conjugates of lupane triterpenoids bound through a 1,2,3-triazole linker with gallate derivatives were prepared via Cu-catalyzed cycloaddition reactions of [3β,28-diacetoxy-20(29)-lupen-30-yl]azide and 3β-acetoxylup-20(29)-en-30-azido-28-oic acid with gallate derivatives with propargyl substituents in various positions. Conjugate 4 based on betulin with a modified gallate substituent containing a dioxolane moiety possessed potent antioxidant properties and anti-inflammatory activity (suppression of NO hyperexpression).