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<p>Hybrid compounds of the furanoditerpenoid type, i.e., <i>N</i>-(arylpyrimidin-2-yl)pyrazole, connected via a methanone linker were synthesized for the first time from methyl phlomisoate. The main synthetic approach was cyclocondensation of diterpenoid alkyne-1,2-diones with 2-hydrazinylpyrimidines. Conditions for selective formation of 3- or 5-(labdanoid)-substituted (arylpyrimidin-2-yl)pyrazoles were proposed. Analgesic activity in thermal and chemical irritation models was found for the new pyrimidine-containing furanoditerpenoids.</p>

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Synthetic Transformations of Higher Terpenoids. 47.* Synthesis of Isomeric 3- or 5-(Furanolabdanoid)-Substituted N-(Pyrimidin-2-yl)Pyrazoles and Assessment of Their Analgesic Activity

  • 期刊论文

  • 发表日期：

    2026年3月1日

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  • M. E. Mironov,
  • A. I. Poltanovich,
  • V. I. Krasnov,
  • S. A. Borisov,
  • T. G. Tolstikova,
  • E. E. Shults

摘要

Hybrid compounds of the furanoditerpenoid type, i.e., N-(arylpyrimidin-2-yl)pyrazole, connected via a methanone linker were synthesized for the first time from methyl phlomisoate. The main synthetic approach was cyclocondensation of diterpenoid alkyne-1,2-diones with 2-hydrazinylpyrimidines. Conditions for selective formation of 3- or 5-(labdanoid)-substituted (arylpyrimidin-2-yl)pyrazoles were proposed. Analgesic activity in thermal and chemical irritation models was found for the new pyrimidine-containing furanoditerpenoids.