953089-09-3

Usage

Uses

Different sources of media describe the Uses of 953089-09-3 differently. You can refer to the following data:
1. An Adenosine (A280400) impurity.
2. An Adenosine (A280400(P)) impurity.

Upstream product

• 108-24-7 acetic anhydride 
• 2140-25-2 5'-O-acetyladenosine 
• 58-61-7 adenosine 
• 31199-61-8 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(dimethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 31281-89-7 2',3',5'-tri-O-acetyl-8-iodoadenosine 
• 23205-65-4 2',3',5'-tri-O-acetyl-8-aminoadenosine 
• 80585-33-7 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-pyrrolidin-1-yl-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 3021-21-4 9-β-D-ribofuranosyl-6-thio-9H-purine 2',3',5'-triacetate 
• 863591-77-9 6-pivaloylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine 
• 906361-01-1 7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)adenine 
• 1574561-33-3 C₁₆H₂₁N₇O₇ 
• 94042-04-3 6-amino-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 2466-76-4 N-Acetylimidazole 
• 66224-66-6 adenine 

Downstream Products

• 88121-73-7 N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 78098-69-8 2',3',5'-tri-O-acetyl-N⁶-cyanoethyl-phenyl-phosphoryladenosine 
• 1054721-79-7 C₂₂H₂₃ClN₅O₉P 
• 78098-70-1 2',3',5'-tri-O-acetyl-N⁶-o-chlorophenyl-cyanoethylphosphoryl-adenosine 
• 78098-64-3 2',3',5'-tri-O-acetyl-N⁶-diphenylphosphoryladenosine 
• 33422-70-7 ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate 
• 1403611-89-1 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(adamantan-1-yl)-6-(cyclohexylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 

Relevant academic research and scientific papers

A method for synthesizing nelarabine

The invention discloses a new method for synthesizing nelarabine. According to the new method for synthesizing nelarabine, vidarabine is taken as a raw material, and acetylization, methoxylation, nitration and reduction reactions are carried out, so that the target product nelarabine is obtained with the total yield of 52%. The new method for synthesizing nelarabine has the greatest advantages that all the prepared nelarabine is beta configuration, and a tedious step of separating isomers in the traditional method is omitted; meanwhile, the raw material is a common chemical material, so that the raw material is available; and the operation is simple and convenient, the column chromatography isolation is not needed to be carried out in the whole course, and industrialization and expanded production are easy to realize.

ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK

Provided are a kind of nucleoside analogue compounds, and compositions comprising these compounds and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via these compounds or the compositions.

Trityl compound and its preparation method and application

The invention relates to triphenylmethyl compounds, a preparation method and applications thereof; and specifically relates to triphenylmethyl compounds as a kinesin spindle protein Eg5 micromolecular inhibitor, a preparation method thereof, and an applic

Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water

A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.

Efficient and green approach for the complete deprotection of O-acetylated biomolecules

A simple, efficient and mild strategy for the complete O-deacetylation of different per-acetylated biomolecules in aqueous media has been described. Different lipases were tested but only the commercial Amano lipase A from Aspergillus Niger catalyzed the complete deprotection of peracetylated α-glucose to glucose in excellent yield. The experimental conditions were tested, in particular the pH effect. The reaction was performed at different pHs considering the only enzymatic process was evaluated at pH 5 and the combination of enzymatic and chemical migration process was evaluated at higher pHs. Finally pH 7 and 25 °C were selected as best conditions. Thus this lipase fully hydrolyzed different peracetylated α-glycopyranosides (glucose, mannose, glucal, galactal) with >99% yields, whereas very good deprotecting yields (75-80%) were achieved for different acetylated β-glycopyranosides (galactose, ribofuranose) under these mild conditions. This strategy was successfully extended to the fully O-selective deprotection of acetylated nucleosides where >99% yield was rapidly obtained. No selectivity was observed for the N-deacetylation in amino acids and peptides.

Synthesis of nelarabine with pure β-anomer through late-stage C-H nitration/nitro-reduction

An efficient and pure β-anomer synthesis of the clinical drug nelarabine from the readily available vidarabine has been achieved for the first time. The C6 amino group of vidarabine was transformed to methoxy group by diazotization/chlorination followed by methoxylation using Na2CO3/MeOH system. The formation of C(2)-N bond was achieved via the highly selective C-H bond functionalization by reacting with 2,2,2-trifluoroacetic anhydride (TFAA) and tetrabutylammonium nitrate. The final product was obtained in total yield of 58.6% by 5 steps-synthesis from vidarabine after the reduction of nitro group to amino group. Moreover, the drug nelarabine could be obtained in 100 grams scale successfully and no chromatography was needed, which made this route more attractive for industrial application.

Stability studies on the newly discovered cyclic form of tRNA N 6-threonylcarbamoyladenosine (ct6A)

A cyclic form of N6-threonylcarbamoyladenosine bearing an oxazolone moiety (ct6A) was discovered very recently at the position 37 in several tRNA sequences. Our study on the synthesized 5′,3′, 2′-O-acetylated derivative of ct6A confirmed high stability of the modified nucleoside under physiological conditions (PBS buffer, pH 7.4) and revealed remarkable stability of the oxazolone ring in acidic (100 mM HCl, pH 1) and basic (0.1 mM NaOH, pH 10) conditions. This feature may allow for the post-synthetic conversion of t6A into ct6A in assembled oligoribonucleotides.

Synthesis of purine and 7-deazapurine nucleoside analogues of 6-N-(4-nitrobenzyl)adenosine; Inhibition of nucleoside transport and proliferation of cancer cells

Human equilibrative nucleoside transporter 1 (hENT1) is a prototypical nucleoside transporter protein ubiquitously expressed on the cell surface of almost all human tissue. Given the role of hENT1 in the transport of nucleoside drugs, an important class of therapeutics in the treatment of various cancers and viral infections, efforts have been made to better understand the mechanisms by which hENT1 modulates nucleoside transport. To that end, we report here the design and synthesis of novel tool compounds for the further study of hENT1. The 7-deazapurine nucleoside antibiotic tubercidin was converted into its 4-N-benzyl and 4-N-(4-nitrobenzyl) derivatives by alkylation at N3 followed by a Dimroth rearrangement to the 4-N-isomer or by fluoro-diazotization followed by SNAr displacement of the 4-fluoro group by a benzylamine. The 4-N-(4-nitrobenzyl) derivatives of sangivamycin and toyocamycin antibiotics were prepared by the alkylation approach. Cross-membrane transport of labeled uridine by hENT1 was inhibited to a weaker extent by the 4-nitrobenzylated tubercidin and sangivamycin analogues than was observed with 6-N-(4-nitrobenzyl)adenosine. Type-specific inhibition of cancer cell proliferation was observed at micromolar concentrations with the 4-N-(4-nitrobenzyl) derivatives of sangivamycin and toyocamycin, and also with 4-N-benzyltubercidin. Treatment of 2′,3′,5′-O-acetyladenosine with aryl isocyanates gave the 6-ureido derivatives but none of them exhibited inhibitory activity against cancer cell proliferation or hENT1.

Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water

A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

Application of the dipeptidyl peptidase IV (DPPIV/CD26) based prodrug approach to different amine-containing drugs

Here we explore the applicability of the dipeptidyl peptidase IV (DPPIV/CD26) based prodrug approach to a variety of amine-containing drugs. Efficient procedures have been developed for the synthesis of dipeptide and tetrapeptide amide prodrugs including