title: Design, synthesis, and antiviral evaluation of purine-β-lactam and purine-aminopropanol hybrids.
abstract: Purine-β-lactam chimera were prepared as a novel class of hybrid systems through N-alkylation of 6-benzylamino- or 6-benzyloxypurine with (ω-haloalkyl)-β-lactams, followed by reductive ring opening of the β-lactam ring by LiEt(3)BH to provide an entry into the class of purine-aminopropanol hybrids. Both new types of hybrid systems were assessed for their antiviral activity and cytotoxicity, resulting in the identification of eight purine-β-lactam hybrids and two purine-aminopropanol hybrids as promising lead structures.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Karen
authors.initials: K
authors.lastname: Mollet
authors.forename: Rob
authors.initials: R
authors.lastname: De Vreese
authors.forename: Tim H M
authors.initials: TH
authors.lastname: Jonckers
authors.forename: Géry
authors.initials: G
authors.lastname: Dams
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D006518:Hepatitis Viruses / Q000187:drug effects; D006801:Humans; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009975:Orthomyxoviridae / Q000187:drug effects; D011412:Propanolamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012328:RNA Viruses / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D007769:Lactams; D011412:Propanolamines; D011687:Purines