RESUMO
Niphathesine C and related pyridine alkaloids are well known natural products with interesting antimicrobial activities, characterized by a pyridine ring and a lipophilic side chain with a terminal nitrogen-containing functional group. This paper describes the synthesis of analogues of these alkylpyridine alkaloids with variation of the heterocyclic ring and the terminal functional group. Key steps of the syntheses are a Sonogashira reaction of appropriate aryl iodides with undec-10-ynol or undec-10-ynoic acid derivatives. The resulting compounds were tested in an agar diffusion assay against several bacteria and fungi.
Assuntos
Alcaloides/síntese química , Alcanos/síntese química , Antibacterianos/síntese química , Antifúngicos/síntese química , Piridinas/síntese química , Alcaloides/farmacologia , Alcanos/farmacologia , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Bactérias/efeitos dos fármacos , Bactérias/crescimento & desenvolvimento , Fungos/efeitos dos fármacos , Fungos/crescimento & desenvolvimento , Testes de Sensibilidade Microbiana , Estrutura Molecular , Piridinas/farmacologiaRESUMO
Polyketide-derived macrolactones like zearalenone (1), zearalane (2) or curvularin (3) display a wide range of interesting pharmacological activities. Here, we present a short and efficient approach towards this class of natural products by a combination of the Sonogashira and Mitsunobu reactions. The resulting lactone 9 was tested against human cancer cell lines at the NCI.