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
• Article Data: 15

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

General Description

Adenosine N1-oxide is a chemical compound that is derived from adenosine, a nucleoside that is a component of DNA and RNA. Adenosine N1-oxide is formed when adenosine is subjected to oxidative stress, such as exposure to reactive oxygen species. It is known to be an important regulator of cellular function, as it can modulate the activity of enzymes and receptors that are involved in various physiological processes. Adenosine N1-oxide has also been found to have potential anti-inflammatory and neuroprotective properties, making it a subject of interest in research related to neurodegenerative diseases and inflammatory conditions. Studies have shown that adenosine N1-oxide may have therapeutic potential in treating conditions such as ischemic brain injury and neuroinflammation, and it continues to be an area of active investigation in the field of biochemistry and pharmacology.

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

• 58-61-7 adenosine 
• 24808-47-7 5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 
• 71724-30-6 1-methoxy adenosine 
• 110526-61-9 5-Amino-N'-methoxy-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 

Downstream Products

• 4105-39-9 2-(methylthio)adenosine 
• 31528-53-7 2-(propylthio)adenosine 
• 13406-51-4 2-methylthio-N⁶-methyladenosine 
• 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 
• 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.

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.

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.