Synthesis and biological evaluation of furopyrimidine N,O-nucleosides.
A series of modified N,O-nucleosides, characterized by the presence of a furopyrimidine moiety, has been synthesized by exploiting a Sonogashira cross coupling reaction of 1-isoxazolidinyl-5-iodouracil with alkynes, followed by treatment with CuI in refluxing TEA/MeOH mixture. The obtained compounds were screened against both RNA and DNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations. However, some of them were able to inhibit proliferation of MRC-5, Vero, BS-C-1 cells by 50% (CC50) at concentrations ranging from 0.7 to 62.5 mM.
Dipartimento di Scienze del Farmaco e Prodotti per la Salute, University of Messina, Italy. robromeo@unime.it
Roberto
R
Romeo
Salvatore V
SV
Giofrè
Adriana
A
Garozzo
Benedetta
B
Bisignano
Antonino
A
Corsaro
Maria A
MA
Chiacchio
D000480:Alkynes / Q000737:chemistry; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002522:Chlorocebus aethiops; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011743:Pyrimidines / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives / Q000737:chemistry; D014709:Vero Cells; D014780:Viruses / Q000187:drug effects
D000480:Alkynes; D000998:Antiviral Agents; D009705:Nucleosides; D011743:Pyrimidines; D014498:Uracil; C048747:5-iodouracil; C030986:pyrimidine
Antiviral activity; Cytotoxicity; Furopyrimidines; N,O-nucleosides; Sonogashira reaction