Synthesis, structure and tumour necrosis factor‐α production‐enhancing properties of novel adamantylamino heterocyclic derivatives

The synthesis of several adamantylated aminoheterocycles is reported. The attack of the adamantyl cation formed from 1‐adamantanol in refluxing trifluoroacetic acid or induced by microwave irradiation provides adamantylamino‐derivatives of respective heterocycles. Adamantylated heterocycles enhance the induction of tumour necrosis factor α (TNF‐α) in genetically modified murine melanoma cells transduced with the gene for human TNF‐α. Of the studied collection of adamantylated compounds, the most biologically active are 2‐adamantylamino‐6‐methylpyridine and 2‐adamantylamino‐4‐methylpyrimidine. The crystal structure of 2‐adamantylamino‐6‐methylpyridine is reported.