Synthesis of 6-arylthio analogs of 2',3'-dideoxy-3'-fluoroguanosine and their effect against hepatitis B virus replication.
A key compound, 2-amino-6-chlor-9-(2,3-dideoxy-3-fluoro-beta-D-erythro-pentofuranosyl)puine, was prepared from 2-amino-6-chloropurine riboside in 5 steps, then subjected to the nucleophilic displacement with benzenethiols to afford 6-arylthio congeners. These compounds showed a similar anti-HBV effect to that of 2',3' dideoxy-3'-fluoroguanosine.
Torii
Takayoshi
T
Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Kanagawa, Japan.
Onishi
Tomoyuki
T
Izawa
Kunisuke
K
Maruyama
Tokumi
T
Demizu
Yosuke
Y
Neyts
Johan
J
De Clercq
Erik
E
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006515:Hepatitis B virus / Q000187:drug effects* / Q000502:physiology; D015394:Molecular Structure; D014779:Virus Replication / Q000187:drug effects*
D000998:Antiviral Agents; D015224:Dideoxynucleosides; C055315:3'-fluoro-2',3'-dideoxyguanosine