title: Stereoselective synthesis of 4'-selenonucleosides via seleno-Michael reaction as potent antiviral agents.
abstract: Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5'-OH for phosphorylation, 4'-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5'-Homo-4'-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.
authors.affiliation: College of Pharmacy, Seoul National University , Seoul, 151-742, Korea.
authors.forename: Pramod K
authors.initials: PK
authors.lastname: Sahu
authors.forename: Gyudong
authors.initials: G
authors.lastname: Kim
authors.forename: Jinha
authors.initials: J
authors.lastname: Yu
authors.forename: Ji Yoon
authors.initials: JY
authors.lastname: Ahn
authors.forename: Jayoung
authors.initials: J
authors.lastname: Song
authors.forename: Yoojin
authors.initials: Y
authors.lastname: Choi
authors.forename: Xing
authors.initials: X
authors.lastname: Jin
authors.forename: Jin-Hee
authors.initials: JH
authors.lastname: Kim
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.forename: Sunghyouk
authors.initials: S
authors.lastname: Park
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018259:Herpesvirus 1, Human / Q000737:chemistry* / Q000187:drug effects; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010766:Phosphorylation; D018139:Simplexvirus / Q000187:drug effects*; D013237:Stereoisomerism; D013937:Thymidine Kinase / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000998:Antiviral Agents; D015224:Dideoxynucleosides; D016566:Organoselenium Compounds; D013937:Thymidine Kinase