Tampere University of Technology

TUTCRIS Research Portal

5 ',5 '-Phosphodiesters and esterase labile triesters of 2 '-C-methylribonucleosides

Research output: Contribution to journalArticleScientificpeer-review

Details

Original languageEnglish
Pages (from-to)226-243
Number of pages18
JournalARKIVOC
Publication statusPublished - 2012
Publication typeA1 Journal article-refereed

Abstract

Bis(2'-C-methyladenosin-5'-yl) (11), bis(2'-C-methylguanosin-5'-yl) (13), bis(2'-C-methyluridin-5'-yl) (15) and 2'-C-methylguanosin-5'-yl 2'-C-methyluridin-5'-yl (16) phosphodiesters have been prepared as pro-drug candidates for the respective 2'-C-methylribonucleoside 5'-monophosphates, expectedly exhibiting antiviral activity against Hepatitis C virus. Additionally, the bis(2'-C-methyladenosine) diester has been converted to 3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl)propyl (19) or pivaloyloxymethyl (20) triester. The underlying idea is that the 5',5'-phosphodiester is first released by intracellular carboxyesterases and subsequently cleaved to nucleoside and nucleoside 5'-monophosphate by phosphodiesterases.

Keywords

  • Pro-drug, antiviral, nucleotide, phosphoester, synthesis, CHRONIC HEPATITIS-C