Compounds > adenosine 2',3'-ribo-epoxide
Page last updated: 2024-12-06

adenosine 2',3'-ribo-epoxide

Description

Adenosine 2',3'-ribo-epoxide is a synthetic analog of adenosine that exhibits potent antitumor activity. It is known to inhibit the growth of various cancer cell lines, including leukemia, lymphoma, and melanoma. This compound is a potent inhibitor of ribonucleotide reductase, an enzyme essential for DNA synthesis. The epoxide group in adenosine 2',3'-ribo-epoxide is crucial for its activity, as it allows the compound to bind to the enzyme and prevent its function. Its mechanism of action involves the formation of a covalent adduct with the enzyme, leading to its inactivation. Research efforts focus on understanding the specific mechanisms of action, optimizing its efficacy, and exploring its potential as a therapeutic agent in cancer treatment.'

adenosine 2',3'-ribo-epoxide: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72252
CHEMBL ID2032007
SCHEMBL ID5471536
MeSH IDM0048959

Synonyms (16)

Synonym
2',3'-epoxya down
2',3'-epoxyadenosine down
2627-64-7
[(1r,2r,4r,5r)-4-(6-aminopurin-9-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methanol
CHEMBL2032007
adenosine, 2',3'-anhydro-
adenosine 2',3'-ribo-epoxide
9-(2,3-anhydro-beta-d-ribofuranosyl)adenine
2',3'-anhydroadenosine
SCHEMBL5471536
RANSNKOSWWZYEJ-KQYNXXCUSA-N
A855616
9-(2,3-anhydropentofuranosyl)-9h-purin-6-amine
DTXSID70949134
[(1r,2r,4r,5r)-4-(6-amino-9h-purin-9-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methanol
((1r,2r,4r,5r)-4-(6-amino-9h-purin-9-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl)methanol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID662565Growth inhibition of Trichomonas vaginalis T1 at 100 uM after 24 hrs by hemocytometry2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine.
AID1065714Trypanocidal activity against bloodstream stage of Trypanosoma brucei brucei AnTat1.1E after 72 hrs by WST-1 assay2013Journal of medicinal chemistry, Dec-27, Volume: 56, Issue:24
Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis.
AID81438Dose required to inhibit cytopathic effect of human immunodeficiency virus replication in MT-4 cells.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID81069Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (40.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's2 (40.00)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: 12.80

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 Index12.80 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.39206-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
metronidazole
Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.		2.0710C-nitro compound;
imidazoles;
primary alcohol		antiamoebic agent;
antibacterial drug;
antimicrobial agent;
antiparasitic agent;
antitrichomonal drug;
environmental contaminant;
prodrug;
radiosensitizing agent;
xenobiotic
puromycin aminonucleoside
3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine: structure in first source. 3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine : Puromycin derivative that lacks the methoxyphenylalanyl group on the amine of the sugar ring.		2.03103'-deoxyribonucleoside;
adenosines
cytidine
[no description available]		2.0310cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cordycepin
[no description available]		2.71303'-deoxyribonucleoside;
adenosines		antimetabolite;
nucleoside antibiotic
2-chloroadenosine
5-chloroformycin A: structure given in first source		2.0810purine nucleoside
2-fluoroadenosine
[no description available]		2.0810adenosines;
organofluorine compound
2-fluoroadenine
2-fluoroadenine : An organofluorine compound that is adenine in which the hydrogen at position 2 (the carbon between the two nitrogens of the pyrimidine ring) is replaced by a fluorine.		2.0810organofluorine compound;
purines		antineoplastic agent
2'-deoxyadenosine
2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source		2.4120purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		2.4820beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
alovudine
[no description available]		1.9710pyrimidine 2',3'-dideoxyribonucleoside
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		1.9710azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		1.9710
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		7.6830adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
3'-azido-2',3'-dideoxy-5-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		1.9710
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.		2.0810purine ribonucleoside;
purines D-ribonucleoside		fungal metabolite
2-aminoadenosine
[no description available]		2.0710purine nucleoside
2-chloroadenine
6-amino-2-chloropurine: RN & structure given in first source		2.0810
2'-fluoro-2'-deoxyadenosine
[no description available]		2.0710
3'-fluoro-3'-deoxyadenosine
3'-fluoro-3'-deoxyadenosine: structure given in first source		2.0710
5'-deoxy-5'-s-isobutylthioadenosine
5'-deoxy-5'-S-isobutylthioadenosine: considered an analog of S-adenosylhomocysteine; structure		2.0710
xylose
xylopyranose: structure in first source		1.9510D-xylose
3'-fluoro-2',3'-dideoxyuridine
[no description available]		1.9710
puromycin
[no description available]		2.0310puromycinsantiinfective agent;
antimicrobial agent;
antineoplastic agent;
EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor;
EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor;
nucleoside antibiotic;
protein synthesis inhibitor
3'-azido-2',3'-dideoxyadenosine
[no description available]		1.9710
3'-azido-2',3'-dideoxycytidine
[no description available]		1.9710
(2R,3S,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-oxolanol
[no description available]		1.97103'-deoxyribonucleoside;
purines
2-chloro-3'-deoxyadenosine
2-chloro-3'-deoxyadenosine: do not confuse with 2-chloro-2'-deoxyadenosine which is CLADRIBINE		2.0810
5'-chloro-5'-deoxyadenosine
[no description available]		2.0710adenosines
2'-amino-2'-deoxyuridine
2'-amino-2'-deoxyuridine: structure in first source		2.0710
5'-amino-5'-deoxyadenosine
[no description available]		2.0710
deoxyguanosine
[no description available]		1.9710purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
inosine
[no description available]		2.0710inosines;
purines D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		01.9710
African Sleeping Sickness
[description not available]		02.0810
Trypanosomiasis, African
A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.		02.0810
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