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

Anna Leisvuori; Zafar Ahmed; Mikko Ora; Lawrence Blatt; Leonid Beigelman; Harri Lönnberg

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

Anna Leisvuori
, Zafar Ahmed
, Mikko Ora
, Lawrence Blatt
, Leonid Beigelman
, Harri Lönnberg

Research output: Contribution to journal › Article › Scientific › peer-review

2 Citations (Scopus)

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.

Original language	English
Pages (from-to)	226-243
Number of pages	18
Journal	Arkivoc
Publication status	Published - 2012
Publication type	A1 Journal article-refereed

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Pro-drug
antiviral
nucleotide
phosphoester
synthesis
CHRONIC HEPATITIS-C

Access to Document

http://www.arkat-usa.org/get-file/44143/

Cite this

@article{89dbffa04b8c442d9914fc8031723d25,

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

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",

author = "Anna Leisvuori and Zafar Ahmed and Mikko Ora and Lawrence Blatt and Leonid Beigelman and Harri L{\"o}nnberg",

note = "EXT=”Ahmed, Zafar”",

year = "2012",

language = "English",

pages = "226--243",

journal = "Arkivoc",

issn = "1551-7004",

publisher = "Arkat",

}

TY - JOUR

T1 - 5 ',5 '-Phosphodiesters and esterase labile triesters of 2 '-C-methylribonucleosides

AU - Leisvuori, Anna

AU - Ahmed, Zafar

AU - Ora, Mikko

AU - Blatt, Lawrence

AU - Beigelman, Leonid

AU - Lönnberg, Harri

N1 - EXT=”Ahmed, Zafar”

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

KW - Pro-drug

KW - antiviral

KW - nucleotide

KW - phosphoester

KW - synthesis

KW - CHRONIC HEPATITIS-C

M3 - Article

SN - 1551-7004

SP - 226

EP - 243

JO - Arkivoc

JF - Arkivoc

ER -

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

Abstract

UN SDGs

Keywords

Access to Document

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