Synthesis and anti-HBV activity of thiouracils linked via S and N-1 to the 5-position of methyl beta-D-ribofuranoside.
Reverse nucleoside derivatives of 2-(methylsulfanyl)uracils 6a-d were prepared by treating of the sodium salt of 2-(methylsulfanyl)uracils (5a-d) with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-beta-D-ribofuranoside (2). The alkylation of 2-thiouracils 4a-d with methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribofuranoside (3) afforded the corresponding S-ribofuranoside derivatives 8a-d. Deisopropylidenation of 6a-d and 8a-d afforded the corresponding deprotected derivatives 7a-d and 9a-d, respectively. The Anti-HBV activity of selected compounds was studied.
Abdel-Rahman
Adel A H
AA
Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt.
Abdel-Megied
Ahmed E S
AE
Goda
Adel E S
AE
Zeid
Ibrahim F
IF
El Ashry
El Sayed H
el SH
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006515:Hepatitis B virus / Q000187:drug effects*; D006801:Humans; D012266:Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D013889:Thiouracil / Q000031:analogs & derivatives* / Q000378:metabolism
D000998:Antiviral Agents; D013889:Thiouracil; D012266:Ribose