6034-68-0

Usage

InChI:InChI=1/C7H7N5O/c1-4(13)12-7-5-6(9-2-8-5)10-3-11-7/h2-3,5H,1H3,(H,8,9,10,11,12,13)

Upstream product

• 108-24-7 acetic anhydride 
• 73-24-5 7H-purin-6-ylamine 
• 108-05-4 vinyl acetate 
• 66224-66-6 adenine 
• 81375-73-7 6-(hydroxyiminomethyleneamino)purine 
• 35803-57-7 ethyl adenosine-5'-carboxylate 
• 82741-17-1 <5',5'-2H2>adenosine 

Downstream Products

• 16370-43-7 ethyl-(7⁽⁹⁾H-purin-6-yl)-amine 
• 1247023-23-9 6-N-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O,4'-C-(N-methylaminomethylene) adenosine 
• 1394229-67-4 C₁₀H₁₁N₅O₂ 
• 105970-01-2 N⁶-acetyl-9-(2-oxopropyl)adenine 
• 147127-20-6 tenofovir 

Relevant academic research and scientific papers

Synthesis of (R) - 9 - (2-hydroxy-propyl) adenine method

The invention discloses a method for synthesizing (R)-9-(2-hydroxy propyl) adenine. The method sequentially comprises the following steps: (1) primary amino acetylation: dissolving adenine in an organic solvent, adding alkali and a catalyst, stirring, and dripping acetic anhydride at 0-10 DEG C; holding at 80-85 DEG C, stirring and reacting for 6-10 h to obtain reaction liquid; (2) N-hydroxy propylation: regulating the pH of the reaction liquid to 9-10, adding propylene carbonate, stirring and reacting at 120-140 DEG C, cooling to 70-80 DEG C, adding toluene, stirring for 2-3 h, and separating and drying to obtain a solid product; (3) deacetylation reaction: adding the solid product into a sodium hydroxide aqueous solution, stirring to react at 90-95 DEG C for 2-4 h, cooling to the room temperature, neutralizing the pH to 6-8 through concentrated hydrochloric acid, separating and drying to obtain the product. The method provided by the invention is used for greatly increasing the reaction selectivity, avoiding the generation of byproduct (R)-6-(2-hydroxy propyl) adenine, increasing the yield of the (R)-9-(2-hydroxy propyl) adenine by more than 90% and greatly lowering the production cost of tenofovir disoproxil fumarate.

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

Some Intramolecular Michael Addition of Adenine Derivatives

In our attempts to prepare polymerizable derivatives of nucleic acid bases, we investigated the reaction of adenine (1) and 9-(cyanoethyl)adenine (4) with acrylic anhydride and acryloyl chloride. reactions of adenine with methyl acrylate and vinyl acrylate were also examined.The results show that these reactions are solvent dependent and the intermediate acryloyladenine 3 can undergo a facile intramolecular Michael reaction to form 7.

Mass Spectrometry of Nucleic Acid Constituents. Trimethylsilyl Derivatives of Nucleosides1,2

Trimethylsilylation of nucleosides provides derivatives which are thermally volatile and whose electron-ionization mass spectra are useful for structural characterization and for determination of chemically or biologically incorporated stable isotopes.The major reaction pathways and mechanisms of fragmentation of silylated nucleosides have been studied, on the basis of the mass spectra of a structural variety of nucleoside analogues and of uridine selectively labeled with deuterium (C-2', C-3', C-5', Si(CD3)3) and oxygen-18 (O2, O4, O-2', O-3', O-5').Formation of most of the major base-containing ions, which are even-electron species, involving rearrangement of hydrogen from the sugar skeleton to the ionized base.The site selectivity of some of the rearrangement processes indicates that base-H-2' interactions are relatively important and that in those cases significant opening of the ribose ring does not occur prior to hydrogen abstraction by the base.The relative abundance of sugar H ions resulting from transfer of H-2' to the base was found to be greater in derivatives of β-ribofuranosides compared with that for the corresponding α anomers, reflecting differences in steric accessibility of H-2' to the base and providing a means of distinguishing α and β anomers.The determination of the site and extent of isotopic substitution in the sugar is better measured from fragment ions which contain the base plus portions of the sugar than from sugar ions which do not contain the base.This is a consequence of the multiple pathways of formation of most sugar-derived ions.

NEW SYNTHETIC APPROACH FOR AZOLOPURINES AND ANALOGS

A new synthetic approach has been developed for the synthesis of some azolopurines, i.e. derivatives of 1,2,4-triazolo(3,4-b)purine (3) and pyrrolo(2,1-b)purine (8), and for some pyrazolo(3,4-d)pyrimidines (12,14).