A1 Refereed original research article in a scientific journal
5 ',5 '-Phosphodiesters and esterase labile triesters of 2 '-C-methylribonucleosides
Authors: Leisvuori A, Ahmed Z, Ora M, Blatt L, Beigelman L, Lonnberg H
Publisher: ARKAT USA INC
Publication year: 2012
Journal: Arkivoc
Journal name in source: ARKIVOC
Journal acronym: ARKIVOC
Issue: 5
First page : 226
Last page: 243
Number of pages: 18
ISSN: 1551-7004
DOI: https://doi.org/10.3998/ark.5550190.0013.520
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/3182820
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.
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.
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