Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents

Byul Nae Yoo; Hea Ok Kim; Hyung Ryong Moon; Su Kyung Seol; Sung Key Jang; Kang Man Lee; Lak Shin Jeong

doi:10.1016/j.bmcl.2006.05.089

Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents

Bioorg Med Chem Lett. 2006 Aug 15;16(16):4190-4. doi: 10.1016/j.bmcl.2006.05.089. Epub 2006 Jun 14.

Authors

Byul Nae Yoo¹, Hea Ok Kim, Hyung Ryong Moon, Su Kyung Seol, Sung Key Jang, Kang Man Lee, Lak Shin Jeong

Affiliation

¹ Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Republic of Korea.

PMID: 16781148
DOI: 10.1016/j.bmcl.2006.05.089

Abstract

On the basis of potent anti-HCV activity of 2'-C-methyladenosine, novel 2'-C-hydroxymethyladenosine analogues 2a-c were synthesized from d-ribose in order to lead to favorable interaction with HCV polymerase. Among compounds tested, adenosine derivative 2a exhibited potent anti-HCV activity, indicating that the hydroxyl group of 2'-C-hydroxymethyl substituent led to favorable interaction with HCV polymerase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antiviral Agents / chemical synthesis*
Antiviral Agents / pharmacology*
Chemistry, Pharmaceutical / methods
DNA-Directed RNA Polymerases / chemistry
Drug Design
Hepacivirus / metabolism*
Hepatitis C / drug therapy*
Models, Chemical
Purine Nucleosides / chemical synthesis*
Purine Nucleosides / therapeutic use
RNA, Viral / chemistry
Ribonucleosides / chemistry

Substances

Antiviral Agents
Purine Nucleosides
RNA, Viral
Ribonucleosides
DNA-Directed RNA Polymerases