n-allyladenosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

N-Allyladenosine (N-Ade) is a nucleoside analog that exhibits a wide range of pharmacological activities. It has been shown to possess anti-inflammatory, analgesic, and neuroprotective properties. N-Ade is synthesized by the allylation of adenosine, a naturally occurring nucleoside. The compound has been shown to inhibit the activity of various enzymes, including adenosine deaminase and phosphodiesterase. This inhibition leads to an increase in adenosine levels, which is known to have beneficial effects on various physiological processes. N-Ade is a promising candidate for the development of new therapeutic agents for various diseases. It is currently being investigated for its potential use in the treatment of inflammatory diseases, pain, and neurodegenerative disorders. Further research is needed to fully understand its mechanisms of action and potential clinical applications.'

Cross-References

ID Source	ID
PubMed CID	97078
CHEMBL ID	1290749
CHEBI ID	165838
SCHEMBL ID	6761791
MeSH ID	M0200548

Synonyms (13)

Synonym
n-allyladenosine
15763-12-9
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-[6-(prop-2-enylamino)purin-9-yl]oxolane-3,4-diol
CHEBI:165838
CHEMBL1290749
n6-allyladenosine
nsc 98777
adenosine, n-2-propenyl-
SCHEMBL6761791
(2r,3r,4s,5r)-2-[6-(allylamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
n-2-propenyl-adenosine
AKOS040753192
adenosine, n-2-propen-1-yl-

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
purine nucleoside
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (30)

Assay ID	Title	Year	Journal	Article
AID90274	Concentration required for 50% growth inhibition of the following cell lines human burkitt lymphoma cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID539777	Cytotoxicity against human J82 cells at 10 uM after 72 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID130975	Antitumor activity against mouse leukemia, L-1210(DBA/2 Ha Mice) % increase in life span at 3.12 mg/kg of dose per day	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID539783	Induction of MMP9 activity in human T24 cells after 1 hr by zymography	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID138630	Antitumor activity against mouse leukemia, L-1210(DBA/2 Ha Mice) mean life span (days) of the mouse after fractionated dosage(dose divided in two halves and administered in two daily injections) at 6.25 mg/kg of dose per day	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID539779	Cytotoxicity against human MDA-MB-231 cells at 10 uM after 72 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID138966	Antitumor activity against slow growing spontaneous mammary tumors in the DBA/2 Ha-DD mouse number of days reacquired fro tumor growth 3.8 mg/kg/day x 5 melphalan once in 5 days	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID539778	Cytotoxicity against human Caco-2 cells at 10 uM after 72 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID138631	Antitumor activity against slow growing spontaneous mammary tumors in the DBA/2 Ha-DD mouse mean life span in days at 50 mg/kg give 5 times once in 5 days	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID139992	Concentration required for 50% growth inhibition of the following cell lines mouse fibro blasts	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID155531	Inhibition of Trypanosoma brucei phosphoglycerate kinase (PGK); inactive at 4 mM	2000	Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22	Adenosine analogues as inhibitors of Trypanosoma brucei phosphoglycerate kinase: elucidation of a novel binding mode for a 2-amino-N(6)-substituted adenosine.
AID539782	Inhibition of human T24 cells invasion on Matrigel after 24 hrs	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID539776	Cytotoxicity against human T24 cells at 10 uM after 72 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID130490	antitumor activity against mouse leukemia, L-1210(DBA/2 Ha Mice) % increase in life span at 3.12 mg/kg of dose per day	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID539781	Growth inhibition of human T24 cells assessed as reduction of cell count after trypsinization at 10 uM after 72 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID130977	Antitumor activity against slow growing spontaneous mammary tumors in the DBA/2 Ha-DD mouse % increased in life span 3.8 mg/kg/day x 5 melphalan + 50 mg/kg/day compound	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID103053	Concentration required for 50% growth inhibition of human breast tumor cells MCF-7 human breast carcinoma cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID25507	HPLC capacity factor (k')	1985	Journal of medicinal chemistry, Nov, Volume: 28, Issue:11	Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID539780	Cytotoxicity against human T24 cells assessed as inhibition of clones formation at 10 uM after 1 week by clonogenic assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID91137	Concentration required for 50% growth inhibition of the following cell lines human fibro blast cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID201887	Concentration required for 50% growth inhibition of the following cell lines sarcoma S-180 cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID130976	Antitumor activity against slow growing spontaneous mammary tumors in the DBA/2 Ha-DD mouse % increased in life span 3.8 mg/kg/day x 5 melphalan + 50 mg/kg/day	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID539784	Inhibition of human T24 cell migration by wound healing assay	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.
AID48652	Concentration required for 50% growth inhibition of the following cell lines Carcinoma TA-3 cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID138629	Antitumor activity against mouse leukemia, L-1210(DBA/2 Ha Mice) mean life span ( days) of the mouse after the dosage at 1.56 mg/kg of dose per day	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID228918	Molar potency ratio was evaluated	1985	Journal of medicinal chemistry, Nov, Volume: 28, Issue:11	Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID201700	Concentration required for 50% growth inhibition of human breast tumor cells SW-613 human breast adenocarcinoma cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID1646835	Activation of human STING expressed in monocytes co-expressing IFN assessed as alkaline phosphatase secretion by SEAP reporter gene assay	2020	Bioorganic & medicinal chemistry letters, 01-15, Volume: 30, Issue:2	Structure activity relationship, 6-modified purine riboside analogues to activate hSTING, stimulator of interferon genes.
AID101497	Concentration required for 50% growth inhibition of the following cell lines Leukemia L-1210 cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
AID89994	Concentration required for 50% growth inhibition of the following cell lines human bladder carcinoma cells	1980	Journal of medicinal chemistry, Dec, Volume: 23, Issue:12	Some short-chain N6-substituted adenosine analogues with antitumor properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (33.33)	18.7374
1990's	1 (16.67)	18.2507
2000's	1 (16.67)	29.6817
2010's	1 (16.67)	24.3611
2020's	1 (16.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.47

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.

Metric	This Compound (vs All)
Research Demand Index	12.47 (24.57)
Research Supply Index	1.95 (2.92)
Research Growth Index	4.42 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.47)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	6 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
6-hydroxyadenosine [no description available]	1.96	1
hyaluronoglucosaminidase kinetin riboside: preferentially induces apoptosis by modulating Bcl-2 family proteins and caspase-3 in cancer cells; structure in first source	2	1	purine nucleoside
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.67	3	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
metrifudil [no description available]	2	1
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.	1.96	1	purine ribonucleoside; purines D-ribonucleoside	fungal metabolite
2-aminoadenosine [no description available]	2	1	purine nucleoside
n(6)-benzyladenosine N(6)-benzyladenosine: RN given refers to parent cpd	2.93	4
6-chloropurine riboside [no description available]	1.96	1
phenylisopropyladenosine [no description available]	1.96	1	aromatic amine; benzenes; hydrocarbyladenosine; purine nucleoside; secondary amino compound	adenosine A1 receptor agonist; neuroprotective agent
6-methylpurine riboside [no description available]	1.96	1
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.	2.38	2	methyladenosine
6-methoxypurine arabinoside [no description available]	1.96	1
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.	1.96	1	hydrocarbyladenosine
n(6)-cyclopentyladenosine [no description available]	2.38	2
n-(1-methyl-2-phenylethyl)adenosine, (s)-isomer [no description available]	1.96	1
1-aminoadenosine 1-aminoadenosine: structure	1.96	1
n(6)-cyclohexyladenosine N(6)-cyclohexyladenosine: structure given in first source; receptors, purinergic P1 agonist	2.67	3
n(6)-(2,2-diphenylethyl)adenosine N(6)-(2,2-diphenylethyl)adenosine: adenosine receptor agonist; structure given in first source	2	1

Condition	Relationship Strength	Studies
Leukemia L 1210 [description not available]	1.95	1
Experimental Neoplasms [description not available]	1.95	1
Bladder Cancer [description not available]	2.05	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.05	1
Anoxemia [description not available]	1.97	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	1.97	1
Acute Disease Disease having a short and relatively severe course.	1.97	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	1.97	1
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	1.97	1

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