title: Synthesis and Antiviral Activity Evaluation of 2',5',5'-Trifluoro-Apiosyl Nucleoside Phosphonic Acid Analogs.
abstract: Racemic synthesis of novel 2',5',5'-trifluoro-apiose nucleoside phosphonic acid analogs were performed as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding (α,α-difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2, and HCMV revealed that the pyrimidine analogues have significant anti-HCMV activity.
authors: a BK-21 Project Team, College of Pharmacy, Chosun University , Kwangju 501-759 , Republic of Korea.
authors: Eunae
authors: E
authors: Kim
authors: a BK-21 Project Team, College of Pharmacy, Chosun University , Kwangju 501-759 , Republic of Korea.
authors: Joon Hee
authors: JH
authors: Hong
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003587:Cytomegalovirus / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010429:Pentoses / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010757:Phosphorous Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014777:Virus Diseases / Q000188:drug therapy
chemical_list: D000998:Antiviral Agents; D009705:Nucleosides; D010429:Pentoses; D010757:Phosphorous Acids; C004983:apiose
keywords: 2′,5′,5′-trifluoro-apiose nucleoside phosphonic acid analogues; Vorbrüggen reaction; antiviral agents