RESUMO
A family of novel bitriazolyl acyclonucleosides were synthesized using a simple and convenient one-step synthetic procedure via the Huisgen reaction by addition of NaN(3) onto triazole nucleosides bearing internal alkynyl groups introduced at the 5-position of the triazole ring. Some of the compounds exhibited interesting antiviral activity against tobacco mosaic virus, demonstrating the importance of the bitriazolyl motif for the observed antiviral activity.
Assuntos
Alcinos/química , Antivirais/síntese química , Nucleosídeos/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/química , Antivirais/toxicidade , Nucleosídeos/síntese química , Nucleosídeos/toxicidade , Azida Sódica/química , Triazóis/químicaRESUMO
Novel N-aryltriazole nucleosides were synthesized via Cu-mediated C-N cross-coupling reaction starting with 3-aminotriazole ribonucleoside and various boronic acids. Two of them exhibited potent apoptosis-related antiproliferative activity against the drug-resistant pancreatic cancer cell line MiaPaCa-2, with an increased potency compared to gemcitabine, the reference treatment for pancreatic cancer. A preliminary SAR study suggests that the appended N-aryl moiety and the substituent at its para-position, as well as the ribose sugar component, contribute considerably to the observed antiproliferative activity.