title: Synthesis and in vitro antiviral activities of [(dihydrofuran-2-yl)oxy]methyl-phosphonate nucleosides with 2-substituted adenine as base.
abstract: The synthesis of [(2',5'-dihydrofuran-2-yl)oxy]methyl-phosphonate nucleosides with a 2-substituted adenine base moiety starting from 2-deoxy-3,5-bis-O-(4-methylbenzoyl)-α-L-ribofuranosyl chloride and 2,6-dichloropurine is described. The key step is the regiospecific and stereoselective introduction of a phosphonate synthon at C(2) of the furan ring. None of the synthesized compounds showed significant in vitro activity against HIV, BVDV, and HBV.
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.|School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.
authors.forename: Fei
authors.initials: F
authors.lastname: Liu
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.|School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.
authors.forename: Yingju
authors.initials: Y
authors.lastname: Liu
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.|School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.
authors.forename: Rui-Gang
authors.initials: RG
authors.lastname: Xu
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.|School of Life Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.
authors.forename: Guifu
authors.initials: G
authors.lastname: Dai
authors.affiliation: Zhengzhou Trade and Industry School, 31 Middle Zhongyuan Road, Zhengzhou 450007, P. R. China.
authors.forename: Liu-Xi
authors.initials: LX
authors.lastname: Zhao
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.|School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.
authors.forename: Yafeng
authors.initials: Y
authors.lastname: Wang
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.|School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China.
authors.forename: Hong-Min
authors.initials: HM
authors.lastname: Liu
authors.affiliation: New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China. fwliu@zzu.edu.cn.|School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China. fwliu@zzu.edu.cn.
authors.forename: Feng-Wu
authors.initials: FW
authors.lastname: Liu
authors.affiliation: Laboratory of Virology and Chemotherapy, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven.
authors.forename: Christophe
authors.initials: C
authors.lastname: Pannecouque
authors.affiliation: Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven. Piet.Herdewijn@rega.kuleuven.be.
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D000225:Adenine / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001908:Diarrhea Viruses, Bovine Viral / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006678:HIV / Q000187:drug effects; D006515:Hepatitis B virus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011684:Purine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000998:Antiviral Agents; D063065:Organophosphonates; D011684:Purine Nucleosides; D000225:Adenine
keywords: 2′,5′-Dihydrofuran phosphonate nucleosides; Antiviral activity; Nucleosides, 2-substituted adenine; Stereoselective syntheses