SrasV1, PubMed, Curation, bibRecord, 001D35

5'-O-masked 2'-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents.

Identifieur interne : 001D35 ( PubMed/Curation ); précédent : 001D34; suivant : 001D36

5'-O-masked 2'-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents.

Auteurs : Masahiro Ikejiri [Japon] ; Takayuki Ohshima ; Keizo Kato ; Masaaki Toyama ; Takayuki Murata ; Kunitada Shimotohno ; Tokumi Maruyama

Source :

Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2007.

RBID : pubmed:17766124

Descripteurs français

KwdFr :
- ARN viral (), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Conformation moléculaire, Désoxyadénosine (), Désoxyadénosine (pharmacologie), Désoxyadénosine (synthèse chimique), Hepacivirus (), Humains, Lignée cellulaire, Prolifération cellulaire (), Relation structure-activité, Réplication virale (), Stéréoisomérie, Tests de sensibilité microbienne.
MESH :
- pharmacologie : Antiviraux, Désoxyadénosine.
- synthèse chimique : Antiviraux, Désoxyadénosine.
- ARN viral, Antiviraux, Conformation moléculaire, Désoxyadénosine, Hepacivirus, Humains, Lignée cellulaire, Prolifération cellulaire, Relation structure-activité, Réplication virale, Stéréoisomérie, Tests de sensibilité microbienne.

English descriptors

KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Line, Cell Proliferation (drug effects), Deoxyadenosines (chemical synthesis), Deoxyadenosines (chemistry), Deoxyadenosines (pharmacology), Hepacivirus (drug effects), Humans, Microbial Sensitivity Tests, Molecular Conformation, RNA, Viral (drug effects), Stereoisomerism, Structure-Activity Relationship, Virus Replication (drug effects).
MESH :
- chemical , chemical synthesis : Antiviral Agents, Deoxyadenosines.
- chemical , chemistry : Antiviral Agents, Deoxyadenosines.
- chemical , drug effects : RNA, Viral.
- chemical , pharmacology : Antiviral Agents, Deoxyadenosines.
- drug effects : Cell Proliferation, Hepacivirus, Virus Replication.
- Cell Line, Humans, Microbial Sensitivity Tests, Molecular Conformation, Stereoisomerism, Structure-Activity Relationship.

Abstract

On the basis of our previous study on antiviral agents against the severe acute respiratory syndrome (SARS) coronavirus, a series of nucleoside analogues whose 5'-hydroxyl groups are masked by various protective groups such as carboxylate, sulfonate, and ether were synthesized and evaluated to develop novel anti-hepatitis C virus (HCV) agents. Among these, several 5'-O-masked analogues of 6-chloropurine-2'-deoxyriboside (e.g., 5'-O-benzoyl, 5'-O-p-methoxybenzoyl, and 5'-O-benzyl analogues) were found to exhibit effective anti-HCV activity. In particular, the 5'-O-benzoyl analogue exhibited the highest potency with an EC(50) of 6.1 microM in a cell-based HCV replicon assay. Since the 5'-O-unmasked analogue (i.e., 6-chloropurine-2'-deoxyriboside) was not sufficiently potent (EC(50)=47.2 microM), masking of the 5'-hydroxyl group seems to be an effective method for the development of anti-HCV agents. Presently, we hypothesize two roles for the 5'-O-masked analogues: One is the role as an anti-HCV agent by itself, and the other is as a prodrug of its 5'-O-demasked (deprotected) derivative.

DOI: 10.1016/j.bmc.2007.08.025
PubMed: 17766124

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Le document en format XML

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<front><div type="abstract" xml:lang="en">On the basis of our previous study on antiviral agents against the severe acute respiratory syndrome (SARS) coronavirus, a series of nucleoside analogues whose 5'-hydroxyl groups are masked by various protective groups such as carboxylate, sulfonate, and ether were synthesized and evaluated to develop novel anti-hepatitis C virus (HCV) agents. Among these, several 5'-O-masked analogues of 6-chloropurine-2'-deoxyriboside (e.g., 5'-O-benzoyl, 5'-O-p-methoxybenzoyl, and 5'-O-benzyl analogues) were found to exhibit effective anti-HCV activity. In particular, the 5'-O-benzoyl analogue exhibited the highest potency with an EC(50) of 6.1 microM in a cell-based HCV replicon assay. Since the 5'-O-unmasked analogue (i.e., 6-chloropurine-2'-deoxyriboside) was not sufficiently potent (EC(50)=47.2 microM), masking of the 5'-hydroxyl group seems to be an effective method for the development of anti-HCV agents. Presently, we hypothesize two roles for the 5'-O-masked analogues: One is the role as an anti-HCV agent by itself, and the other is as a prodrug of its 5'-O-demasked (deprotected) derivative.</div>
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5'-O-masked 2'-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents.

5'-O-masked 2'-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents.

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