146-92-9

Basic information

• Product Name: adenosine N1-oxide
• Synonyms: adenosine N1-oxide;adenosine N(sup 1)-oxide;1-Oxylatoadenosine-1-ium;Adenosine 1-oxide;1-Oxoadenosine
• CAS NO: 146-92-9
• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 283.24072
• EINECS: 205-683-0
• Mol File: 146-92-9.mol

Chemical Properties

• Boiling Point: 726°Cat760mmHg
• Flash Point: 392.9°C
• Appearance: /
• Density: 2.15g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.911
• CAS DataBase Reference: adenosine N1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: adenosine N1-oxide(146-92-9)
• EPA Substance Registry System: adenosine N1-oxide(146-92-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• WGK Germany: 3
• Hazardous Substances Data: 146-92-9(Hazardous Substances Data)

Usage

Uses

Used in Neurodegenerative Disease Research:
Adenosine N1-oxide is used as a potential therapeutic agent for neurodegenerative diseases due to its neuroprotective properties. It has shown promise in treating conditions such as ischemic brain injury and neuroinflammation, making it an area of active investigation in the field of biochemistry and pharmacology.
Used in Inflammatory Condition Research:
Adenosine N1-oxide is used as a potential anti-inflammatory agent in research related to inflammatory conditions. Its ability to modulate the activity of enzymes and receptors involved in physiological processes makes it a promising candidate for the development of treatments for various inflammatory disorders.
Used in Biochemical and Pharmacological Research:
Adenosine N1-oxide is used as a subject of interest in biochemical and pharmacological research to explore its potential therapeutic applications. Studies are ongoing to understand its role in cellular function and its potential to modulate the activity of enzymes and receptors, which could lead to the development of new treatments for various diseases and conditions.

InChI:InChI=1/C10H13N5O5/c11-8-5-9(13-3-15(8)19)14(2-12-5)10-7(18)6(17)4(1-16)20-10/h2-4,6-7,10,16-18H,1,11H2/t4-,6-,7-,10-/m1/s1

Upstream product

• 110526-61-9 5-Amino-N'-methoxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 
• 24808-47-7 5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 
• 109923-44-6 5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine Hydrochloride 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 58-61-7 adenosine 
• 71724-30-6 1-methoxy adenosine 

Downstream Products

• 43157-49-9 2-Allylthioadenosine 
• 43157-50-2 2-Thioadenosine 
• 70333-82-3 2-thiomethyl-D-allo-N⁶-threonylcarbamoyladenosine 
• 70333-82-3 2-thiomethyl-L-N⁶-threonylcarbamoyladenosine 
• 950673-11-7 2-(cyclohexylethylthio)adenosine 
• 13406-51-4 2-methylthio-N⁶-methyladenosine 
• 31528-53-7 2-(propylthio)adenosine 
• 4105-39-9 2-(methylthio)adenosine 
• 43157-50-2 2-Mercaptoadenosine 
• 41111-71-1 1-oxy-O^{2'_,O3'_{-phenylboranediyl-O}5'}-(toluene-4-sulfonyl)-adenosine 
• 151566-00-6 2-(6-amino-2-(p-nitrophenylethyl)sulfanyl-7H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 
• 148527-86-0 2-<(phenylethyl)thio>adenosine 
• 43157-47-7 2-(Cyclohexylthio)adenosine 

Relevant articles and documents

2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5′-nucleotidase (CD73) Inhibitors with Variable Binding Modes

CD73 inhibitors are promising drugs for the (immuno)therapy of cancer. Here, we present the synthesis, structure-activity relationships, and cocrystal structures of novel derivatives of the competitive CD73 inhibitor α,β-methylene-ADP (AOPCP) substituted in the 2-position. Small polar or lipophilic residues increased potency, 2-iodo- and 2-chloro-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (15, 16) being the most potent inhibitors with Ki values toward human CD73 of 3-6 nM. Subject to the size and nature of the 2-substituent, variable binding modes were observed by X-ray crystallography. Depending on the binding mode, large species differences were found, e.g., 2-piperazinyl-AOPCP (21) was >12-fold less potent against rat CD73 compared to human CD73. This study shows that high CD73 inhibitory potency can be achieved by simply introducing a small substituent into the 2-position of AOPCP without the necessity of additional bulky N6-substituents. Moreover, it provides valuable insights into the binding modes of competitive CD73 inhibitors, representing an excellent basis for drug development.

Chemical Synthesis of Oligoribonucleotide (ASL of tRNALys T. brucei) Containing a Recently Discovered Cyclic Form of 2-Methylthio-N6-threonylcarbamoyladenosine (ms2ct6A)

The synthesis of the protected form of 2-methylthio-N6-threonylcarbamoyl adenosine (ms2t6A) was developed starting from adenosine or guanosine by using the optimized carbamate method and, for the first time, an isocyanate route. The hypermodified nucleoside was subsequently transformed into the protected ms2t6A-phosphoramidite monomer and used in a large-scale synthesis of the precursor 17nt ms2t6A-oligonucleotide (the anticodon stem and loop fragment of tRNALys from T. brucei). Finally, stereochemically secure ms2t6A→ms2ct6A cyclization at the oligonucleotide level efficiently afforded a tRNA fragment bearing the ms2ct6A unit. The applied post-synthetic approach provides two sequentially homologous ms2t6A- and ms2ct6A-oligonucleotides that are suitable for further comparative structure–activity relationship studies.

New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors

Currently approved platelet adenosine diphosphate (ADP) receptor antagonists target only the platelet P2Y12 receptor. Moreover, especially in patients with acute coronary syndromes, there is a strong need for rapidly acting and reversible antiplatelet agents in order to minimize the risk of thrombotic events and bleeding complications. In this study, a series of new P1,P4-di(adenosine-5′) tetraphosphate (Ap4A) derivatives with modifications in the base and in the tetraphosphate chain were synthesized and evaluated with respect to their effects on platelet aggregation and function of the platelet P2Y1, P2Y12, and P2X1 receptors. The resulting structure-activity relationships were used to design Ap4A analogs which inhibit human platelet aggregation by simultaneously antagonizing both P2Y1 and P2Y12 platelet receptors. Unlike Ap4A, the analogs do not activate platelet P2X1 receptors. Furthermore, the new compounds exhibit fast onset and offset of action and are significantly more stable than Ap4A to degradation in plasma, thus presenting a new promising class of antiplatelet agents.

ORAL WASHING COMPOSITION FOR PREVENTING AND/OR TREATING PERIODONTAL DISEASES

The present invention has an object to provide a mouthwash composition for preventing and/or treating periodontal diseases safely and effectively. The present invention solves the above abject by providing a mouthwash composition for preventing and/or treating periodontal diseases, characterized in that it comprises, as an effective ingredient(s), one or more members selected from the group consisting of adenosine N1-oxide, 3'-glucosyladenosine N1-oxide, 5'-glucosyladenosine N1-oxide, 5'-adenosine diphosphate N1-oxide, and 5'-adenosine triphosphate N1-oxide but does not contain any saccharide assimilable by periodontal disease bacteria.

THERAPEUTIC AGENT FOR INFLAMMATORY DISEASES CONTAINING ADENOSINE N1-OXIDE AS ACTIVE INGREDIENT

The present invention has an object to provide an effective and safe therapeutic agent for inflammatory diseases such as sepsis, hepatitis, and inflammatory bowel disease, and solves the above object by providing a therapeutic agent for inflammatory diseases containing adenosine N1-oxide or a derivative thereof as an effective ingredient.

Nucleoside-5′-monophosphates as prodrugs of adenosine A2A receptor agonists activated by ecto-5′-nucleotidase

Prodrugs of adenosine A2A receptor agonists were developed that are activated by ecto-5′-nucleotidase (ecto-5′-NT,CD73). Because ecto-5′-NT is upregulated in inflamed tissue, the A2A agonists are expected to be released from their prodrug form at the sites of inflammation. 2-(Ar)alkyl-substituted AMP derivatives were synthesized and investigated. Certain 2-substituted AMP derivatives, including 2-hexylthio-AMP, 2-cyclopentylthio-AMP, 2-cyclohexylmethylthio-AMP, and 2-cyclohexylethylthio-AMP were accepted as substrates by ecto-5′-NT and readily converted to the corresponding 2-substituted adenosine derivatives. The 2-cyclohexylethylthio substitution was a good compromise between the requirements of the ecto-5′-NT and the adenosine A2A receptor. The corresponding AMP derivative (12g) was a similarly good substrate as AMP itself, while the resulting adenosine derivative (11g) was a relatively potent A2A agonist (radioligand binding to rat brain striatal membranes: Ki=372 nM; inhibition of anti-CD3/anti-CD28-induced IFN-γ release in mouse CD4+ cells: EC50=50 nM). Compound 11g was released from 12g by incubation with CD4+ cells isolated from wild-type mice but only to a much smaller extent by cells from ecto-5′-NT knockout mice. Compound 12g will be a new lead structure for the development of more potent and selective ecto-5′-NT- activated prodrugs of selective anti-inflammatory A2A receptor agonists.

PHOSPHORYLATED A2A RECEPTOR AGONISTS

A phosphorylated A2A receptor agonist providing agonist properties on the A2A receptor after dephosphorylation the phosphorylated A2A receptor agonist comprises a ribosyl moiety and a purine moiety and being phosphorylated at the 5'-position of the ribose moiety except adenosine monophosphate (AMP), adenosine diphosphate (ADP) or adenosine triphosphate (ATP), a medicament containing the compound of the invention including ADP and the use of the compound of the invention including ATP and ADP for several medical indications e. g. inflammatory events. In particular, compounds of formula (I) are also disclosed.

Synthesis and antiviral evaluation of analogs of adenosine-N1-oxide and 1-(benzyloxy)adenosine

The activity of a series of compounds related to adenosine-N1-oxide (1) and 1-(benzyloxy)adenosine (42) against vaccinia virus has been determined both in vitro and in a vaccinia mouse tailpox model. Significant activities have been found both in vitro and in vivo for a number of the synthetic compounds.

AN IMPROVED PROCEDURE FOR THE PREPARATION OF AROMATIC HETEROCYCLIC N-OXIDES

An improved procedure for the preparation of aromatic heterocyclic N-oxide is described.Nitrogen containing heterocyclic compounds gave their N-oxides in excellent yields by the reaction of m-CPBA in DMF/MeOH in the presence of HF in a short time under mild reaction conditions.The presence of HF and MeOH is crucial for the reaction.

Reactions of 9-substituted 1-aminoadenines with nucleophiles and syntheses of 3-substituted 3H-imidazo[4,5-e][1,2,4]triazolo[1,5-c][1,2,3]triazines

Reactions of 1-aminoadenines (2) with NH2OH gave adenine 1-oxides (6). Alkaline treatment of 2 afforded 5-amino-4-(1,2,4-triazol-3-yl)imidazoles (3), which were converted to 3H-imidazo[4,5-e][1,2,4]triazolo[1,5- c][1,2,3]triazines (5), aza analogues of 3H-[1,2,4]triazolo[3,2-i]purines (4), by treatment with NaNO2.