title: Exploring the purine core of 3'-C-ethynyladenosine (EAdo) in search of novel nucleoside therapeutics.
abstract: A series of new nucleoside analogues based on a C-3 branched ethynyl sugar derivative as present in 3'-C-ethynylcytidine (ECyd) and -adenosine (EAdo), combined with modified purine bases was synthetized and evaluated against a broad array of viruses and tumour cell lines. The pronounced cytostatic activity of EAdo was confirmed. EAdo and its 2,6-diaminopurine analogue showed inhibitory activity against vaccinia virus (EC50: 0.31 and 51 μM, respectively). Derivative 10 on the other hand was found active against varicella zoster virus (EC50: 4.68 μM).
authors.affiliation: Laboratory for Medicinal Chemistry, Ghent University, Ottergemsesteenweg 460, B-9000 Ghent, Belgium.
authors.forename: Fabian
authors.initials: F
authors.lastname: Hulpia
authors.affiliation: KU Leuven, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium.
authors.forename: Jan
authors.initials: J
authors.lastname: Balzarini
authors.affiliation: KU Leuven, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium.
authors.forename: Dominique
authors.initials: D
authors.lastname: Schols
authors.affiliation: KU Leuven, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium.
authors.forename: Graciela
authors.initials: G
authors.lastname: Andrei
authors.affiliation: KU Leuven, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium.
authors.forename: Robert
authors.initials: R
authors.lastname: Snoeck
authors.affiliation: Laboratory for Medicinal Chemistry, Ghent University, Ottergemsesteenweg 460, B-9000 Ghent, Belgium. Electronic address: Serge.VanCalenbergh@ugent.be.
authors.forename: Serge
authors.initials: S
authors.lastname: Van Calenbergh
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D014645:Herpesvirus 3, Human / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D011687:Purines / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: C000612660:3'-C-ethynyladenosine; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D011687:Purines; D000241:Adenosine; C030985:purine
keywords: 3′-C-Ethynyladenosine; Nucleosides; Vorbrüggen coupling