10299-44-2

Basic information

• Product Name: 8-AZAADENOSINE
• Synonyms: 3-beta-d-ribofuranosyl-3h-1,2,3-triazolo(4,5-d)pyrimidin-7-amine;3-triazolo(4,5-d)pyrimidin-7-amine,3-beta-d-ribofuranosyl-3h-2;5-d)pyrimidine,7-amino-3-beta-d-ribofuranosyl-3h-v-triazolo(;8-AZAADENOSINE;3H-v-Triazolo[4,5-d]pyrimidine, 7-amino-3-.beta.-D-ribofuranosyl-;3-β-D-Ribofuranosyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-amine;3H-1,2,3-Triazolo(4,5-D)pyrimidin-7-amine, 3-beta-D-ribofuranosyl-;3H-V-Triazolo(4,5-D)pyrimidine, 7-amino-3-beta-D-ribofuranosyl- (8ci)
• CAS NO: 10299-44-2
• Molecular Formula: C₉H₁₂N₆O₄
• Molecular Weight: 268.23
• Mol File: 10299-44-2.mol

Chemical Properties

• Melting Point: 218-219 °C(Solv: water (7732-18-5))
• Boiling Point: 702.6 °C at 760 mmHg
• Flash Point: 378.7 °C
• Appearance: /
• Density: 2.29 g/cm³
• Vapor Pressure: 1.01E-20mmHg at 25°C
• Refractive Index: 2
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 12.79±0.70(Predicted)
• CAS DataBase Reference: 8-AZAADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-AZAADENOSINE(10299-44-2)
• EPA Substance Registry System: 8-AZAADENOSINE(10299-44-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 10299-44-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-AZAADENOSINE is used as a substrate for adenosine kinase, an enzyme that plays a crucial role in the regulation of adenosine levels in the body. Its interaction with adenosine kinase makes it a valuable compound for studying the enzyme's function and potential therapeutic applications.
Used in Research and Development:
8-AZAADENOSINE is used as a research tool to investigate the role of adenosine in various biological processes. Its unique structure allows for the study of hydrogen bonding and other molecular interactions, providing insights into the mechanisms of adenosine action and its potential as a therapeutic target.
Used in Drug Design:
The unique properties of 8-AZAADENOSINE make it a promising candidate for the development of new drugs targeting adenosine-related pathways. Its ability to interact with adenosine kinase and other molecular targets can be leveraged to design novel therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C9H12N6O4/c10-7-4-8(12-2-11-7)15(14-13-4)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H2,10,11,12)

Upstream product

• 116599-50-9 N-(1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-acetamide 
• 109451-10-7 O^2'_,O3'_,O5'-triacetyl-2-methylsulfanyl-8-aza-adenosine 
• 53458-40-5 8-Aza-2',3'-O-isopropylidene-adenosine 
• 92516-90-0 2',3',5'-tri-O-acetyl-8-azaadenosine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 4471-88-9 N⁶-nonanoyl-8-azaadenine 
• 5975-09-7 2,3-O-isopropylidene-β-D-ribofuranosyl-1-azide 
• 149355-96-4 5-O-benzyl-2,3-O-isopropylidene-1-azido-β-D-ribofuranose 
• 149355-98-6 5'-O-benzyl-2',3'-O-isopropylidene-8-azaadenosine 
• 149355-97-5 9-(5'-O-benzyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-azahypoxanthine 
• 67-56-1 methanol 
• 99249-20-4 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carbonitrile 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 

Downstream Products

• 4968-68-7 3-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one 
• 53458-40-5 8-Aza-2',3'-O-isopropylidene-adenosine 
• 588698-74-2 3-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one 

Relevant articles and documents

Novel trypanocidal analogs of 5′-(methylthio)-adenosine

The purine nucleoside 5′-deoxy-5′-(hydroxyethylthio)-adenosine (HETA) is an analog of the polyamine pathway metabolite 5′-deoxy-5′- (methylthio)-adenosine (MTA). HETA is a lead structure for the ongoing development of selectively targeted trypanocidal agents. Thirteen novel HETA analogs were synthesized and examined for their in vitro trypanocidal activities against bloodstream forms of Trypanosoma brucei brucei LAB 110 EATRO and at least one drug-resistant Trypanosoma brucei rhodesiense clinical isolate. New compounds were also assessed in a cell-free assay for their activities as substrates of trypanosome MTA phosphorylase. The most potent analog in this group was 5′-deoxy-5′-(hydroxyethylthio)-tubercidin, whose in vitro cytotoxicity (50% inhibitory concentration [IC50], 10 nM) is 45 times greater than that of HETA (IC50, 450 nM) against pentamidine-resistant clinical isolate KETRI 269. Structure-activity analyses indicate that the enzymatic cleavage of HETA analogs by trypanosome MTA phosphorylase is not an absolute requirement for trypanocidal activity. This suggests that additional biochemical mechanisms are associated with the trypanocidal effects of HETA and its analogs. Copyright

Studies on structure of kinetin riboside and its analogues by variable-temperature NMR

Kinetin riboside and its four base-modified analogues were synthesized and their structures in solution were examined by multinuclear 1D and 2D variable-temperature NMR techniques. At lowered temperature kinetin riboside was found to exist as a mixture of two distinct conformers resulting from the restricted rotation around the C6-N6 bond. For 8-azakinetin riboside and 2-fluorokinetin riboside the presence of two rotamers was observed at room temperature.

Cyclic dinucleotide compound, preparation method and application thereof

The invention discloses a cyclic dinucleotide compound, a preparation method and an application thereof, specifically, the invention relates to a compound of a formula (I), a pharmaceutically acceptable salt thereof, the preparation method thereof, and the application in the preparation of a medicine for treatment and/or prevention of a disease associated with activation of STING protein or as a vaccine adjuvant. The diseases associated with activation of the STING protein include viral infections, bacterial infections, cancers, diseases related to the immune system, and the like.

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

C6-substituted analogues of 8-azanebularine: Probes of an RNA-editing enzyme active site

We describe the synthesis of derivatives of 8-azanebularine, a known inhibitor of adenosine deaminases including the RNA-editing enzyme ADAR2. 6-Methyl, 6-hydroxymethyl, 6-cyano, and 6-mercapto derivatives were obtained from 6-bromo precursors using diffe

8-Azaadenosine and its 2'-deoxyribonucleoside: Synthesis and oligonucleotide base-pair stability

The synthesis of 8-azaadenosine (1a; z8A) has been performed by SnCl4- catalyzed glycosylation of 8-azaadenine (4) with 1,2,3,5-tetra-O-acetyl-β- D-ribofuranose (5), followed by the separation of the regioisomers 6 an d7 and subsequent deacetylation. The ribonucleoside 1a as well as its 2'-deoxy derivative 1b (z8A(d)) were converted into oligonucleotide building blocks- the phosphonate 2 as well as the phosphoramidites 3 and 19. They were used to prepare the oligoribonucleotide (z8A-U)6 and oligodeoxyribonucleotides. The T(m) values and the thermodynamic data of duplex formation of the modified duplexes showed no significant changes compared to those containing A(d) or A residues. This indicates that the stereoelectronic effect of the 8-azaadenine base which was found for the monomeric nucleoside has only a minor influence on the duplex stability.

Evaluation of the quantitative contribution of an aryl group on C(2) of 8-azaadenines to binding with adenosine deaminase: A new synthesis of 8-azaadenosine. XI

The introduction of a phenyl group on C(2) of 8-azaadenosine increases binding to the adenosine deaminase enzyme (ADA). This stability increment has been quantitatively evaluated in both 8-azaadenosines and 9-(2',3'-dihydroxypropyl)-8-azaadenines; it resulted nearly equivalent in the two series. 8-Azaadenosine has been synthesized through a new route employing fully protected β-D-ribofuranosyl-1-azide. Instead, the stability difference in 9-(n-alkyl)-8-azaadenines, owing to the inactivity of the C(2) unsubstituted compounds, could not be evaluated. Consideration of the enantioselectivity of the ADA enzyme toward chiral 9-(2',3'-dihydroxypropyl)-8-azaadenines and 9-(2',3'-dihydroxypropyl)-8-azahypoxanthines allowed the exclusion of an appreciable structural modification in the enzyme-inhibitor complex when hydrogen on C(2) is substituted by an aryl group.