Page last updated: 2024-11-08

2'-c-methyladenosine

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Description

2'-C-methyladenosine: antiviral [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID500900
CHEMBL ID73809
SCHEMBL ID382543
MeSH IDM0570237

Synonyms (32)

Synonym
2-c-methyl adenosine
2'-methyl-adenosine
2'-c-methyladenosine
2'-c-methyl adenosine
CHEMBL73809 ,
beta-2'-methyladenosine
(2r,3r,4r,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
2'-c-methyl-adenosine
bcx-4026
2'-c-mea
2'-c-ch3-a
(3r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
2'-c-me-a
2''-c-methyladenosine
(2r,3r,4r,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
2''-methyl-adenosine
bdbm50144948
(2r,3r,4r,5r)-5-hydroxymethyl-3-methyl-2-(6-methylamino-purin-9-yl)-tetrahydro-furan-3,4-diol
beta-2''-methyladenosine
(2r,3r,4r,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
15397-12-3
AKOS015914550
(2r,3r,4r,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
PASOFFRBGIVJET-YRKGHMEHSA-N
SCHEMBL382543
DTXSID90333334
2/'-c-methyladenosine
mfcd02682944
F12904
BS-25234
PD077382
2-c-methyladenosine

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" 2'-C-Methyladenosine was found to be susceptible to enzymatic conversions by adenosine deaminase and purine nucleoside phosphorylase, and it displayed limited oral bioavailability in the rat."( Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
Ball, RG; Bennett, CF; Bera, S; Bhat, B; Bhat, N; Bosserman, M; Brooks, J; Burlein, C; Carroll, SS; Colwell, LF; Cook, PD; Dande, P; Eldrup, AB; Fay, JF; Flores, OA; Getty, K; LaFemina, RL; Leone, J; MacCoss, M; McMasters, DR; Olsen, DB; Prakash, TP; Prhavc, M; Song, Q; Tomassini, JE; Von Langen, D; Wolanski, B, 2004
)
1.23
" The oral bioavailability of the initial lead was below 5%; therefore, additional analogues were synthesized and screened for liver NTP levels after oral administration to rats."( Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.
Boyer, SH; Erion, MD; Fujitaki, JM; Hecker, SJ; Huang, W; Koeplinger, KA; Linemeyer, DL; MacCoss, M; Olsen, DB; Reddy, KR; Reddy, MV; Sun, Z; van Poelje, PD; Varkhedkar, V, 2007
)
0.64

Dosage Studied

ExcerptRelevanceReference
" Lead compounds identified in a primary rat hepatocyte screen were shown to result in liver levels of NTP predictive of efficacy after intravenous dosing to rats."( Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.
Boyer, SH; Erion, MD; Fujitaki, JM; Hecker, SJ; Huang, W; Koeplinger, KA; Linemeyer, DL; MacCoss, M; Olsen, DB; Reddy, KR; Reddy, MV; Sun, Z; van Poelje, PD; Varkhedkar, V, 2007
)
0.64
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.74000.00011.20929.9700AID31854
Adenosine receptor A1Bos taurus (cattle)Ki0.93000.00000.71316.0000AID239456; AID32002
Adenosine receptor A2aHomo sapiens (human)Ki4.61000.00001.06099.7920AID239486; AID33928
RNA-directed RNA polymerase IC50 (µMol)1.90000.01902.52798.8000AID86858
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H1 receptorCavia porcellus (domestic guinea pig)EC50 (µMol)0.30000.00260.53341.2020AID86857
RNA-directed RNA polymerase EC50 (µMol)0.30000.00180.23482.8000AID86857
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (50)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A1Bos taurus (cattle)
response to purine-containing compoundAdenosine receptor A1Bos taurus (cattle)
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (93)

Assay IDTitleYearJournalArticle
AID237857Oral bioavailability in rat2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID245909Cytotoxicity against HB-1 cells in an MTS-based assay2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID299924Cytotoxicity against Huh7 cells after 24 hrs by MTS assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine.
AID31854Inhibition of [3H]CHA (N6-cyclohexyl adenosine) to rat brain membrane Adenosine A1 receptor2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.
AID634090Antiviral activity against HCV genotype 1b infected in human HuH7 cells after 3 days by renilla luciferase reporter assay2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
The design, synthesis and biological evaluations of C-6 or C-7 substituted 2-hydroxyisoquinoline-1,3-diones as inhibitors of hepatitis C virus.
AID340156Antitumor activity against human MCF7 cells after 48 hrs by MTS assay2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.
AID673224Cytotoxicity against human HuH7 cells assessed as cell viability at 0.5 uM after 3 days by CellTiter Glo assay2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
C-6 aryl substituted 4-quinolone-3-carboxylic acids as inhibitors of hepatitis C virus.
AID673222Antiviral activity at Hepatitis C virus genotype 1b infected in human HuH7 cells assessed as inhibition of viral replication at 0.5 uM after 3 days by renilla luciferase reporter gene assay2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
C-6 aryl substituted 4-quinolone-3-carboxylic acids as inhibitors of hepatitis C virus.
AID634091Cytotoxicity against human HuH7 cells infected with HCV1b after 3 days by MTS assay2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
The design, synthesis and biological evaluations of C-6 or C-7 substituted 2-hydroxyisoquinoline-1,3-diones as inhibitors of hepatitis C virus.
AID545678Antiviral activity against at 0.3 MOI Dengue virus 2 infected in human A549 cells assessed as level of E protein after 48 hrs by ELISA2010Antimicrobial agents and chemotherapy, Jul, Volume: 54, Issue:7
Inhibition of dengue virus RNA synthesis by an adenosine nucleoside.
AID662447Cytotoxicity against human HuH7 cells after 24 hrs by MTS assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID573112Cytotoxicity against human Huh5-2 cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID658632Oral bioavailability in rat2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
Hepatitis C RNA-dependent RNA polymerase inhibitors: a review of structure-activity and resistance relationships; different scaffolds and mutations.
AID634089Cytotoxicity against human HuH7 cells infected with HCV1b assessed as cell viability at 10 uM after 3 days by MTS assay2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
The design, synthesis and biological evaluations of C-6 or C-7 substituted 2-hydroxyisoquinoline-1,3-diones as inhibitors of hepatitis C virus.
AID410593Antiviral activity against HCV in ET cells assessed as activity of luciferase reporter by subgenomic RNA replicon assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro.
AID246255Inhibition of hepatitis C virus RNA replication in a subgenomic replicon cell line2005Bioorganic & medicinal chemistry letters, Feb-01, Volume: 15, Issue:3
Synthesis of 9-(2-beta-C-methyl-beta-d-ribofuranosyl)-6-substituted purine derivatives as inhibitors of HCV RNA replication.
AID662514Oral bioavailability in rat2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID340154Antitumor activity against human CaCo2 cells after 48 hrs by MTS assay2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.
AID237085Half-life in rats2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID410597Selectivity index, EC50 for HCV to IC50 for ET cells2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro.
AID546790Antiviral activity against Hepatitis C virus genotype 1a in luciferase encoding genotype 1a replicons after 3 days by luciferase reporter assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Novel hepatitis C virus reporter replicon cell lines enable efficient antiviral screening against genotype 1a.
AID296868Activation of prodrug to corresponding nucleoside triphosphate in Sprague-Dawley rat hepatocytes at 25 uM after 2 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.
AID236601Cmax value in rats2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID299922Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 24 hrs by ribonuclease protection assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine.
AID662449Stability of the compound assessed as compound remaining at 10 uM after 60 mins in presence of bovine adenosine deaminase2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID248027In vitro inhibitory activity against human colon carcinoma HT-29 cell line2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Antitumor activity of C-methyl-beta-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors.
AID233377Inhibitory selectivity at Adenosine 2A receptor compared to Adenosine 1 receptor.1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.
AID243038Relative affinities against adenosine A2A and A1 receptors (ratio of KiA2A/KiA1)2005Journal of medicinal chemistry, Mar-10, Volume: 48, Issue:5
Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.
AID233379Inhibitory selectivity at Adenosine A3 receptor compared to Adenosine 2A receptor.1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.
AID662446Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed as cytoprotection after 24 hrs2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID326174Antiviral activity against Hepatitis C virus 1b after 3 days2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Synthesis, cytostatic and anti-HCV activity of 6-(N-substituted aminomethyl)-, 6-(O-substituted hydroxymethyl)- and 6-(S-substituted sulfanylmethyl)purine nucleosides.
AID255673Effective concentration required to reduce Hepatitis C virus2005Journal of medicinal chemistry, Sep-08, Volume: 48, Issue:18
Cytostatic 6-arylpurine nucleosides. 6. SAR in anti-HCV and cytostatic activity of extended series of 6-hetarylpurine ribonucleosides.
AID545677Cytotoxicity against human A549 cells assessed as intracellular ATP level by Celltiter-Glo luminescent assay2010Antimicrobial agents and chemotherapy, Jul, Volume: 54, Issue:7
Inhibition of dengue virus RNA synthesis by an adenosine nucleoside.
AID262678Antiviral activity against BVDV NADL in MDBK cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and anti-BVDV activity of acridones as new potential antiviral agents.
AID634088Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed as reduction in luciferase activity at 10 uM after 3 days2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
The design, synthesis and biological evaluations of C-6 or C-7 substituted 2-hydroxyisoquinoline-1,3-diones as inhibitors of hepatitis C virus.
AID247910In vitro inhibitory activity against human leukemia K562IU cell line2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Antitumor activity of C-methyl-beta-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors.
AID33491Selectivity towards Adenosine A3 receptor to Adenosine A2A receptor2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.
AID573110Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH6 cells assessed as reduction in replicon RNA after 4days by RT-qPCR analysis2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID239486Displacement of [3H]CGS-21680 binding to adenosine A2A receptors of bovine striatal membranes2005Journal of medicinal chemistry, Mar-10, Volume: 48, Issue:5
Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.
AID33494Displacement of [3H](R)-PIA from Adenosine A3 receptor of rat testis membrane with 150 nM DPCPX at 10e-5 M2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.
AID573106Cytotoxicity against human Huh-9-13 cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID248110In vitro inhibitory activity against human myelogenous leukemia K562 cell line2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Antitumor activity of C-methyl-beta-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors.
AID315592Cytotoxicity against human Huh7 cells harboring con1 replicon after 3 days by MTT assay2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides.
AID573108Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh5-2 cells assessed as reduction in replicon RNA after 4 days by luciferase assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID1638600Antiviral activity against West Nile virus2019Journal of medicinal chemistry, 03-14, Volume: 62, Issue:5
DDX3X Helicase Inhibitors as a New Strategy To Fight the West Nile Virus Infection.
AID262680Selectivity index (CC50/EC50) for inhibition of BVDV NADL in MDBK cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and anti-BVDV activity of acridones as new potential antiviral agents.
AID662448Inhibition of HCV genotype 1b NS5B after 90 mins2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID340155Antitumor activity against human HT29 cells after 48 hrs by MTS assay2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.
AID326175Cytotoxicity against human Huh7 cells after 3 days by MTT method2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Synthesis, cytostatic and anti-HCV activity of 6-(N-substituted aminomethyl)-, 6-(O-substituted hydroxymethyl)- and 6-(S-substituted sulfanylmethyl)purine nucleosides.
AID244278Percent displacement of [125I]AB-MECA binding to adenosine A3 receptors of bovine cortical membranes at 0.00005 M2005Journal of medicinal chemistry, Mar-10, Volume: 48, Issue:5
Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.
AID491244Cytotoxicity against human Huh7 cells after 3 days by WST-1 assay2010Bioorganic & medicinal chemistry, Jul-01, Volume: 18, Issue:13
Synthesis and anti-hepatitis C virus (HCV) activity of 3'-C-substituted-methyl pyrimidine and purine nucleosides.
AID35021Affinity to Adenosine A2A receptor of rat brain striatum using [3H]-CGS- 216802002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.
AID237656Clearance in rats when administered at a dose of 1 mg/kg i.v. and 2 mg/mL p.o.2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID261902Cytotoxicity against Huh7 cells by MTS assay2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Synthesis and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methyl purine nucleosides as inhibitors of hepatitis C virus RNA replication.
AID432569Antiviral activity against HCV by viral replicon assay2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus.
AID239456Displacement of [3H]DPCPX binding to adenosine A1 receptors of bovine cortical membranes2005Journal of medicinal chemistry, Mar-10, Volume: 48, Issue:5
Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.
AID326173Cytostatic activity in human HeLa S3 cells assessed as inhibition of cell growth after 48 hrs by XTT assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Synthesis, cytostatic and anti-HCV activity of 6-(N-substituted aminomethyl)-, 6-(O-substituted hydroxymethyl)- and 6-(S-substituted sulfanylmethyl)purine nucleosides.
AID86858Inhibition HCV NS5B-mediated RNA synthesis2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.
AID246173Inhibition of HCV RNA replication in a subgenomic bicistronic replicon assay in HB-1 cells2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID86857Inhibition HCV RNA replication2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.
AID432564Antiviral activity against HCV assessed as inhibition of viral replicon replication in human Huh5-2 cells2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus.
AID299923Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 72 hrs by ribonuclease protection assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine.
AID33928Inhibitory activity at Adenosine A2A receptor by inhibition of [3H]-CGS- 21680 binding to bovine striatal membranes.1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.
AID261901Antiviral activity against HCV replication2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Synthesis and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methyl purine nucleosides as inhibitors of hepatitis C virus RNA replication.
AID573107Cytotoxicity against human Huh-Mono cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID262679Cytotoxicity against MDBK cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and anti-BVDV activity of acridones as new potential antiviral agents.
AID432565Cytotoxicity against human Huh5-2 cells2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus.
AID262697Antiviral activity against VP32947-resistant BVDV in MDBK cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and anti-BVDV activity of acridones as new potential antiviral agents.
AID673229Antiviral activity at Hepatitis C virus genotype 1b infected in human HuH7 cells assessed as inhibition of viral replication at 0.5 uM after 3 days by quantitative RT-PCR analysis2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
C-6 aryl substituted 4-quinolone-3-carboxylic acids as inhibitors of hepatitis C virus.
AID33019Selectivity for Adenosine A2A over Adenosine A1 receptor2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.
AID236960Tmax value in rats2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID410595Cytotoxicity against ET cells2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro.
AID233378Inhibitory selectivity at Adenosine A3 receptor compared to Adenosine 1 receptor.1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.
AID32002Inhibitory activity at Adenosine A1 receptor by inhibition of [3H]CHA binding to bovine brain cortical membranes.1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.
AID573111Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-Mono cells assessed as reduction in replicon RNA after 4 days by RT-qPCR analysis2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID662513Plasma clearance in rat2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.
AID247671Compound was tested for the inhibition of HCV NS5B-mediated RNA synthesis2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.
AID243033Relative affinities for adenosine A3 and A1 receptors (ratio of KiA3/KiA1)2005Journal of medicinal chemistry, Mar-10, Volume: 48, Issue:5
Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.
AID248043In vitro inhibitory activity against human breast carcinoma MCF-7 cell line2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Antitumor activity of C-methyl-beta-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors.
AID255627Cytotoxic concentration required to reduce the rRNA level of hepatitis C virus2005Journal of medicinal chemistry, Sep-08, Volume: 48, Issue:18
Cytostatic 6-arylpurine nucleosides. 6. SAR in anti-HCV and cytostatic activity of extended series of 6-hetarylpurine ribonucleosides.
AID1502482Antiviral activity against Dengue virus 2 New Guinea assessed as inhibition of virus induced cytopathic effect by neutral red dye uptake assay2017ACS medicinal chemistry letters, Sep-14, Volume: 8, Issue:9
Anchimerically Activatable Antiviral ProTides.
AID491243Antiviral activity against HCV genotype1 infected in human Huh7 cells assessed as reduction of viral replication by steady-Glo luciferase assay2010Bioorganic & medicinal chemistry, Jul-01, Volume: 18, Issue:13
Synthesis and anti-hepatitis C virus (HCV) activity of 3'-C-substituted-methyl pyrimidine and purine nucleosides.
AID573109Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-9-13 cells assessed as reduction in replicon RNA after 4days by RT-qPCR analysis2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID33490Selectivity for Adenosine A3 over Adenosine A1 receptor2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.
AID315591Antiviral activity against HCV 1b Con1 replicon in Huh7 cells2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides.
AID546789Antiviral activity against Hepatitis C virus genotype 1b in luciferase encoding genotype 1b replicons after 3 days by luciferase reporter assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Novel hepatitis C virus reporter replicon cell lines enable efficient antiviral screening against genotype 1a.
AID245982Cytotoxicity concentration to inhibit hepatitis C virus RNA replication in a subgenomic replicon cell line2005Bioorganic & medicinal chemistry letters, Feb-01, Volume: 15, Issue:3
Synthesis of 9-(2-beta-C-methyl-beta-d-ribofuranosyl)-6-substituted purine derivatives as inhibitors of HCV RNA replication.
AID340153Antitumor activity against human K562 cells after 48 hrs by MTS assay2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.
AID573105Cytotoxicity against human HuH6 cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID634092Therapeutic index, ratio of CC50 for human HuH7 cells infected with HCV1b to EC50 for HCV genotype 1b2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
The design, synthesis and biological evaluations of C-6 or C-7 substituted 2-hydroxyisoquinoline-1,3-diones as inhibitors of hepatitis C virus.
AID33330Inhibitory activity against Adenosine A3 receptor by inhibition of [3H](R)-PIA binding to rat testis membranes1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.
AID243039Relative affinities for adenosine A2A and A3 receptors (ratio of KiA2A/KiA3)2005Journal of medicinal chemistry, Mar-10, Volume: 48, Issue:5
Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.
AID262698Selectivity index (CC50/EC50) for inhibition of VP32947-resistant BVDV in MDBK cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and anti-BVDV activity of acridones as new potential antiviral agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.70)18.2507
2000's17 (45.95)29.6817
2010's17 (45.95)24.3611
2020's2 (5.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.24

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.24 (24.57)
Research Supply Index3.64 (2.92)
Research Growth Index5.94 (4.65)
Search Engine Demand Index13.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other35 (94.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]