Synthesis, structure and tumour necrosis factor-alpha production-enhancing properties of novel adamantylamino heterocyclic derivatives
Mauri, J.K.; Lasek, W.; Górska, A.; Switaj, T.; Wamil, M.; Młynarczuk, I.; Kazimierczuk, Z.
Anti-Cancer Drug Design 16(2-3): 73-80
2001
ISSN/ISBN: 0266-9536 PMID: 11962515 Document Number: 535198
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 alpha (TNF-alpha) in genetically modified murine melanoma cells transduced with the gene for human TNF-alpha. Of the studied collection of adamantylated compounds, the most biologically active are 2-adamantylamino-6-methylpyridine and 2-adamantylamino4-methylpyrimidine. The crystal structure of 2-adamantylamino-6-methylpyridine is reported.