17318-24-0

Usage

Uses

Used in Pharmaceutical Industry:
3',5'-DI-O-ACETYL-2'-DEOXYADENOSINE is used as an intermediate for the synthesis of anti-hepatitis C virus agents. Its role in the development of these agents is significant, as it contributes to the overall effectiveness of the final product in combating the hepatitis C virus.

Upstream product

• 4958-66-1 N⁶,O^3',O^5'-triacetyl-2'-deoxyadenosine 
• 88091-71-8 3',5'-di-O-acetyl N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine 
• 108-24-7 acetic anhydride 
• 958-09-8 2'-deoxy-D-adenosine 
• 79-21-0 peracetic acid 
• 763103-09-9 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(2-trimethylsilanyl-ethoxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 

Downstream Products

• 72560-67-9 5'-O-acetyl-2'-deoxyadenosine 
• 6612-73-3 3'-O-acetyl-2'-deoxyadenosine 
• 958-09-8 2'-deoxy-D-adenosine 
• 763103-10-2 (9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 91593-00-9 triethylammonium 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-p-nitrophenylethyl-phosphate 
• 91608-32-1 2'-deoxy-5'-O-(4-monomethoxytrityl)-N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine 
• 91592-98-2 N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate 
• 91592-97-1 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate 
• 922713-73-3 N⁶-(N-p-chlorophenyl-carbamoyl)-3',5'-di-O-acetyl-2'-deoxyadenosine 
• 922713-78-8 N⁶-(N-p-methylphenyl-carbamoyl)-3',5'-di-O-acetyl-2'-deoxyadenosine 
• 37113-47-6 (-)-N⁶-(benzyl)-2'-deoxyadenosine 
• 25775-85-3 N⁶-(2-Isopentenyl)-2'-deoxyadenosine 
• 16006-64-7 6-methyl-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 
• 1430099-60-7 N⁶-di(tert-butyl)(isobutyl)silyl-5'-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 

Relevant academic research and scientific papers

Ribose-modified adenosine analogues as potential partial agonists for the adenosine receptor

We have adopted a practical three-step route for the synthesis of 2'- and 3'-deoxy analogues of N6-substituted adenosines: protection of the hydroxyl groups, replacement of the N6-amino by a better leaving group, and combined deprote

SELECTIVE N-DEACYLATION OF N,O-PROTECTED NUCLEOSIDES BY ZINC BROMIDE

N-Acyl protecting group in nucleoside derivatives can be selectively removed by treatment with zinc bromide in the presence of alcohols to give O-protected nucleosides.

Spectral assignments and reference data complete1H and 13C NMR spectral assignment of α- And β-adenosine, 2′-deoxyadenosine and their acetate derivatives

1H and 13C NMR chemical shifts of α- and β-anomers of adenosine, 2′-deoxyadenosine and their acetate derivatives were completely and definitely assigned using the concerted application of one- and two-dimensional experiments (gCOSY, gNOESY, gHSQC and gHMBC). The influence of the stereochemistry of the purine base on the NMR data of the hydrogen and carbon atoms of the furanose moiety was estimated. Copyright

Synthesis of fluorescent adenosine analogues

In the synthesis of a transition state inhibitor of the enzyme adenylosuccinate lyase two different [2,1-i]-pyrimido-purine derivatives are formed, of which one might be very interesting for cell biological research, due to its strong fluorescent properties.

Amino Acid Modified RNA Bases as Building Blocks of an Early Earth RNA-Peptide World

Fossils of extinct species allow us to reconstruct the process of Darwinian evolution that led to the species diversity we see on Earth today. The origin of the first functional molecules able to undergo molecular evolution and thus eventually able to create life, are largely unknown. The most prominent idea in the field posits that biology was preceded by an era of molecular evolution, in which RNA molecules encoded information and catalysed their own replication. This RNA world concept stands against other hypotheses, that argue for example that life may have begun with catalytic peptides and primitive metabolic cycles. The question whether RNA or peptides were first is addressed by the RNA-peptide world concept, which postulates a parallel existence of both molecular species. A plausible experimental model of how such an RNA-peptide world may have looked like, however, is absent. Here we report the synthesis and physicochemical evaluation of amino acid containing adenosine bases, which are closely related to molecules that are found today in the anticodon stem-loop of tRNAs from all three kingdoms of life. We show that these adenosines lose their base pairing properties, which allow them to equip RNA with amino acids independent of the sequence context. As such we may consider them to be living molecular fossils of an extinct molecular RNA-peptide world.

APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT

PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT

DNA binding and cleavage studies of copper(II) complexes with 2′-deoxyadenosine modified histidine moiety

This work is focused on the study of DNA binding and cleavage properties of 2′-deoxyadenosines modified with ester/amide of histidine (his6dA ester, his6dA amide) and their copper(II) complexes. To determine the coordination mode of

Trifluoromethyl derivatives of canonical nucleosides: Synthesis and bioactivity studies

The use of the system CF3SO2Na/tert-butyl- hydroperoxide (tert-ButOOH), recently reported for the efficient trifluoromethylation of a variety of heterocyclic aromatic compounds, has been here profitably exploited for the synthesis of 5-CF3-2′- deoxycytidine, 8-CF3-2′-deoxyadenosine, 8-CF 3-2′-deoxyguanosine and 8-CF3-inosine, regioselectively obtained in good to acceptable yields following a very simple protocol. The bioactivity of these modified nucleosides, and particularly of the novel 8-CF3-2′-deoxyguanosine and 8-CF3-inosine, has been evaluated on a panel of tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays.

N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF

The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF

The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.