title: Novel acyclic phosphonylated 1,2,3-triazolonucleosides with an acetamidomethyl linker: synthesis and biological activity.
abstract: A new series of 4-substituted [(1,2,3-triazol-1-yl)acetamido]methylphosphonates as acyclic nucleotide analogs were synthesized from diethyl (2-chloroacetamido)methylphosphonate via azidation followed by 1,3-dipolar cycloaddition with selected alkynes derived from natural nucleobases or their mimetics. All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3-triazol-1-yl)acetamido]methylphosphonate 6e substituted with the N(3)-Bz-benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.
authors.affiliation: Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź, Poland.
authors.forename: Iwona E
authors.initials: IE
authors.lastname: Głowacka
authors.forename: Jan
authors.initials: J
authors.lastname: Balzarini
authors.forename: Andrzej E
authors.initials: AE
authors.lastname: Wróblewski
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002415:Cats; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D061565:Cycloaddition Reaction; D003588:Cytopathogenic Effect, Viral; D004267:DNA Viruses / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012328:RNA Viruses / Q000187:drug effects; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000081:Acetamides; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009711:Nucleotides; D063065:Organophosphonates; D014230:Triazoles
keywords: Antiviral; Cycloaddition; Synthesis; Triazoles