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

: Leisvuori A, Ahmed Z, Ora M, Blatt L, Beigelman L, Lonnberg H

Publisher: ARKAT USA INC

: 2012

: Arkivoc

: ARKIVOC

: 5

: 226

: 243

: 18

: 1551-7004

DOI: https://doi.org/10.3998/ark.5550190.0013.520(external)

: https://research.utu.fi/converis/portal/detail/Publication/3182820(external)

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.

Chemical sciences

5-5-phosphodiesters-and-esterase-labile-triesters-of-2-c.pdf