Synthesis of 2'-beta-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors.
Coupling reaction of 2-beta-C-methyl-1,2,3,4-tetra-O-benzoyl-d-ribofuranose with 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine, followed by debromination and debenzoylation, gave the 2'-beta-C-methyl toyocamycin in high yield. Based on this result, a series of 2'-beta-C-methyl-4-substituted toyocamycin and sangivamycin analogues were synthesized for biological screening as potential inhibitors of HCV RNA replication.
Ding
Yili
Y
Valeant Pharmaceuticals, Inc., 3300 Hyland Avenue, Costa Mesa, CA 92626, USA. yding@icnpharm.com
An
Haoyun
H
Hong
Zhi
Z
Girardet
Jean-Luc
JL
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis*; D016174:Hepacivirus; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D012093:Replicon / Q000187:drug effects; D013329:Structure-Activity Relationship; D014127:Toyocamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides; C005699:sangivamycin; D000241:Adenosine; D014127:Toyocamycin