TY - JOUR
T1 - Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C- substituted-methyl pyrimidine and purine nucleosides
AU - Choi, Won Jun
AU - Kim, Yu Min
AU - Kim, Hea Ok
AU - Lee, Hyuk Woo
AU - Kim, Dong Eun
AU - Park, Kwang Su
AU - Chong, Youhoon
AU - Jeong, Lak Shin
PY - 2010
Y1 - 2010
N2 - On the basis of potent anti-hepatitis C virus (HCV) activity of 2′-C-hydroxymethyladenosine, 3′-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from d-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N3, or F) at the 3′-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3′-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents.
AB - On the basis of potent anti-hepatitis C virus (HCV) activity of 2′-C-hydroxymethyladenosine, 3′-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from d-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N3, or F) at the 3′-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3′-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents.
KW - 3′-C-Azidomethyl nucleosides
KW - 3′-C-Fluoromethyl nucleosides
KW - 3′-C-Hydroxymethyl nucleosides
KW - Anti-hepatitis C virus (HCV) activity
KW - Neighboring group effect
UR - http://www.scopus.com/inward/record.url?scp=77954214576&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2010.05.002
DO - 10.1016/j.bmc.2010.05.002
M3 - Article
C2 - 20627592
AN - SCOPUS:77954214576
SN - 0968-0896
VL - 18
SP - 4812
EP - 4820
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 13
ER -
