Author:

Keywords:

Science & Technology, Life Sciences & Biomedicine, Physical Sciences, Chemistry, Medicinal, Chemistry, Organic, Pharmacology & Pharmacy, Chemistry, C5-Alkynyl pyranonucleosides, Microwave-irradiation, Sonogashira coupling reaction, Cytotoxic activity, NUCLEOSIDE ANALOGS, THYMIDINE KINASE, Alkynes, Animals, Antineoplastic Agents, Drug Screening Assays, Antitumor, Female, HeLa Cells, Humans, Leukemia L1210, Mice, Microwaves, Pyrimidine Nucleosides, Uterine Cervical Neoplasms, Hela Cells, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, 1115 Pharmacology and Pharmaceutical Sciences, Medicinal & Biomolecular Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A microwave-assisted, one-pot, coupling reaction for the synthesis of C5-alkynyl-uracil and cytosine glucopyranonucleosides has been developed. The reaction is carried out under standard Sonogashira coupling conditions from glucopyranonucleosides of 5-iodouracil or 5-iodocytosine and various terminal alkynes. All compounds were evaluated for their cytostatic and antiviral activity. The 5-phenylethynyluracil pyranonucleoside derivative 6a showed the most promising cytostatic activity (50% inhibitory concentration in the lower micromolar range). No meaningful antiviral activity was recorded.