[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.13160/ricns.2015.8.3.153

Synthesis and Antiviral Activity Evaluation of 5',5'-Difluoro-2'-methylapiosyl Nucleoside Phosphonic Acid Analogs

Hong, Joon Hee (BK-21 Project Team, College of Pharmacy, Chosun University)

Publication Information

Journal of Integrative Natural Science / v.8, no.3, 2015 , pp. 153-163 More about this Journal

Abstract

Racemic synthesis of novel 5',5'-difluoro-2'-methyl-apiose nucleoside phosphonic acid analogs was achieved as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding ( ${\alpha},{\alpha}$ -difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the pyrimidine analogs (cytosine, uracil, and thymine) have weak anti-HIV or HCMV activity.

Keywords

Antiviral Agents; 5',5'-Difluoro-2'-methyl-apiose Nucleoside Phosphonic Acid Analogues; Vorbruggen Reaction;

Citations & Related Records

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