Compounds > 6-methylpurine riboside
Page last updated: 2024-11-07

6-methylpurine riboside

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Description

6-methylpurine riboside, also known as N6-methyl adenosine, is a nucleoside analog that has been studied for its potential therapeutic applications. It has been shown to exhibit antiviral, anticancer, and immunomodulatory activities. Synthesis of 6-methylpurine riboside can be achieved through various chemical methods, including the methylation of adenosine or the direct glycosylation of 6-methylpurine. The antiviral activity of 6-methylpurine riboside is attributed to its ability to inhibit the replication of viruses, such as HIV and influenza. Its anticancer activity is linked to its potential to induce apoptosis in cancer cells. 6-methylpurine riboside's immunomodulatory effects include the modulation of cytokine production and the activation of immune cells. Researchers are interested in studying 6-methylpurine riboside because of its diverse biological activities and potential therapeutic benefits.'
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6-methylpurine riboside: cpd not in Chemline 6/30/83 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID97131
CHEMBL ID1269736
SCHEMBL ID1682931
MeSH IDM0105200
PubMed CID168266029
MeSH IDM0105200

Synonyms (24)

Synonym
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-(6-methylpurin-9-yl)tetrahydrofuran-3,4-diol
2-hydroxymethyl-5-(6-methyl-purin-9-yl)-tetrahydro-furan-3,4-diol
14675-48-0
6-methylpurine-beta-d-ribonucleoside
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-(6-methylpurin-9-yl)oxolane-3,4-diol
CHEMBL1269736
nsc 101619
6-methyl-9-beta-d-ribofuranosylpurine
6-methyl-9beta-d-ribofuranosylpurine
9h-purine, 6-methyl-9-beta-d-ribofuranosyl-
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-(6-methyl-9h-purin-9-yl)tetrahydrofuran-3,4-diol
AKOS016006085
6-methylpurine-beta-d-riboside, 6-d-mpr
(2s,3r,4s,5s)-2-(hydroxymethyl)-5-(6-methyl-9h-purin-9-yl)-tetrahydrofuran-3,4-diol;
SCHEMBL1682931
mfcd00056009
F12891
FIGBCBGMUIGJBD-PNHWDRBUSA-N
6-methyl-9-(beta-d-ribofuranosyl)purine
BS-25573
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-(6-methyl-9h-purin-9-yl)oxolane-3,4-diol
6-methylpurine riboside
CS-0210962
HY-W154568
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID528343Cytotoxicity against human HeLaS3 cells after 7 hrs by celltiter-glo assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID63948Tested for minimum cytotoxic concentration on virus-induced cytopathicity in E6SM cells1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.
AID634636Cytotoxicity against human CCRF-CEM cells after 72 hrs by coulter counting2012European journal of medicinal chemistry, Jan, Volume: 47, Issue:1
Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides.
AID1272197Prodrug activation assessed as recombinant Trichomonas vaginalis PNP-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
AID64120Tested for minimum inhibitory concentration against Vaccinia virus in E6SM cells1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.
AID228918Molar potency ratio was evaluated1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID528353Antiviral activity against Poliovirus infected in human HeLaS3 cells assessed as frequency of viral mutagenesis plaque at 1.62 uM by guanidine resistance assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID528345Cytotoxicity against human HeLaS3 cells after 48 hrs by celltiter-glo assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID87284Tested for minimum inhibitory concentration against RSV (respiratory syncytial virus) in HeLa cells1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.
AID1272195Prodrug activation assessed as recombinant Escherichia coli PNP-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
AID634635Activity of Escherichia coli PNP assessed per mg of protein at 100 uM by UV spectrometric analysis2012European journal of medicinal chemistry, Jan, Volume: 47, Issue:1
Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides.
AID528344Cytotoxicity against human HeLaS3 cells after 24 hrs by celltiter-glo assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID64122Tested for minimum inhibitory concentration against vesicular stomatitis virus (VSV) in E6SM cells.1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.
AID1272193Prodrug activation assessed as recombinant human PNP-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
AID1272198Prodrug activation assessed as recombinant Sulfolobus solfataricus MTAP-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
AID64118Tested for minimum inhibitory concentration against HSV-1 (KOS strain) in E6SM cells1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.
AID528347Antiviral activity against Dengue virus type 2 in BHK-21 cells assessed as inhibition of viral replication after 24 hrs by luciferase assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID87145Tested for minimum cytotoxic concentration on RSV (respiratory syncytial virus)-induced cytopathicity in HeLa cells1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.
AID528354Antiviral activity against Poliovirus infected in human HeLaS3 cells assessed as frequency of viral mutagenesis plaque at 3.24 uM by guanidine resistance assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID1272199Prodrug activation assessed as recombinant Escherichia coli SAH/MTA hydrolase-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
AID528346Antiviral activity against Poliovirus infected in human HeLaS3 cells assessed as inhibition of viral replication treated 1 hr before infection measured after 2 days2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
AID1272196Prodrug activation assessed as recombinant Escherichia coli PNP M64V mutant-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
AID1272200Prodrug activation assessed as Francisella tularensis PNP-mediated compound cleavage at 100 uM by reverse phase HPLC analysis2016European journal of medicinal chemistry, Jan-27, Volume: 1086-Methylpurine derived sugar modified nucleosides: Synthesis and in vivo antitumor activity in D54 tumor expressing M64V-Escherichia coli purine nucleoside phosphorylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (27.27)18.7374
1990's3 (27.27)18.2507
2000's2 (18.18)29.6817
2010's3 (27.27)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.94

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.94 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tubercidin
Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.		2.0510antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
ribonucleoside		antimetabolite;
antineoplastic agent;
bacterial metabolite
6-hydroxyadenosine
[no description available]		1.9610
3-deazaadenosine
3-deazaadenosine: RN given refers to parent cpd.		1.9810
ribavirin
Rebetron: Rebetron is tradename		2.41201-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.7130adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
nebularine
nebularine: structure. nebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.		1.9610purine ribonucleoside;
purines D-ribonucleoside		fungal metabolite
6-chloropurine riboside
[no description available]		1.9610
phenylisopropyladenosine
[no description available]		1.9610aromatic amine;
benzenes;
hydrocarbyladenosine;
purine nucleoside;
secondary amino compound		adenosine A1 receptor agonist;
neuroprotective agent
n-allyladenosine
[no description available]		1.9610purine nucleoside
n-methyladenosine
N-methyladenosine: is a inhibitor of cell differentiation. N(6)-methyladenosine : A methyladenosine compound with one methyl group attached to N(6) of the adenine nucleobase.		1.9610methyladenosine
ribavirin 5'-triphosphate
ribavirin 5'-triphosphate: structure given in first source. ribavirin 5'-triphosphate : A 1-ribosyltriazole that is ribavirin in which the hydroxy group at the 5'-position is replaced by a triphosphate group. It is the active metabolite of the antiviral agent ribavirin.		2.05101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide;
ribose triphosphate		antiviral agent;
drug metabolite;
EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor;
eukaryotic initiation factor 4F inhibitor;
human blood serum metabolite
6-methoxypurine arabinoside
[no description available]		1.9610
n(6),n(6)-dimethyladenosine
N(6),N(6)-dimethyladenosine : A methyladenosine compound with two methyl groups attached to N(6) of the adenine nucleobase.		1.9610hydrocarbyladenosine
brivudine
brivudine: anti-herpes agent		1.9810
fludarabine
[no description available]		2.0710purine nucleoside
n(6)-cyclopentyladenosine
[no description available]		1.9610
n-(1-methyl-2-phenylethyl)adenosine, (s)-isomer
[no description available]		1.9610
1-aminoadenosine
1-aminoadenosine: structure		1.9610
n(6)-cyclohexyladenosine
N(6)-cyclohexyladenosine: structure given in first source; receptors, purinergic P1 agonist		1.9610
inosine
[no description available]		2.1310inosines;
purines D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
bromide
Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)		210halide anion;
monoatomic bromine
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0110metal allergen;
nickel group element atom;
platinum group metal atom
nebularine
nebularine: structure. nebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.		1.9910purine ribonucleoside;
purines D-ribonucleoside		fungal metabolite
6-methylpurine 2'-deoxyriboside
[no description available]		1.9610
6-methylpurine
6-methylpurine : Purine bearing a methyl substituent at position 6.		2.8940purinesEC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
2,6-dichloropurine
[no description available]		2.0110
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Neoplasms
[description not available]		02.4420
B16 Melanoma
[description not available]		01.9810
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9710