title: Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters.
abstract: Di-aryl nucleoside phosphotriesters have been explored as a new type of pronucleotides for the purpose of anti-HIV-1 therapy and efficient synthetic protocols, based on H-phosphonate chemistry, have been developed for the preparation of this class of compounds. It was found that anti-HIV-1 activity of the phosphotriesters bearing an antiviral nucleoside moiety (AZT, ddA) and also ddU was due, at least partially, to intracellular conversion into the corresponding nucleoside 5'-monophosphates, and their efficiency correlated well with the pK(a) values of the aryloxy groups present.
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Romanowska
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Szymańska-Michalak
authors.forename: Jerzy
authors.initials: J
authors.lastname: Boryski
authors.forename: Jacek
authors.initials: J
authors.lastname: Stawiński
authors.forename: Adam
authors.initials: A
authors.lastname: Kraszewski
authors.forename: Roberta
authors.initials: R
authors.lastname: Loddo
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Sanna
authors.forename: Gabriella
authors.initials: G
authors.lastname: Collu
authors.forename: Barbara
authors.initials: B
authors.lastname: Secci
authors.forename: Paolo
authors.initials: P
authors.lastname: La Colla
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002478:Cells, Cultured; D006678:HIV / Q000502:physiology; D006801:Humans; D006880:Hydroxy Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
chemical_list: D019380:Anti-HIV Agents; D006880:Hydroxy Acids; D009705:Nucleosides; D009711:Nucleotides; D063065:Organophosphonates