4261-14-7

Usage

Uses

Used in Pharmaceutical Industry:
9-BENZYLADENINE is used as a chemical intermediate for the synthesis of various 1-substituted adenines, which are essential in the development of pharmaceutical products. Its role in the synthesis process is crucial for creating compounds with potential therapeutic applications.
Used in Chemical Research:
9-BENZYLADENINE is also utilized in chemical research as a starting material for the development of new compounds with potential applications in various fields, including medicine, agriculture, and materials science. Its unique chemical properties make it a valuable tool for researchers in the field.

Safety Profile

Experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of NOx.

Upstream product

• 58469-93-5 N⁴-benzyl-pyrimidine-4,5,6-triyltriamine; sulfate 
• 77287-34-4 formamide 
• 64-18-6 formic acid 
• 109923-43-5 5-Amino-1-benzyl-1H-imidazole-4-carboxamidine Hydrochloride 
• 40428-86-2 sodium adeninate 
• 100-44-7 benzyl chloride 
• 66224-66-6 adenine 
• 111267-85-7 1-amino-9-benzyl-6-iminopurine 
• 100-39-0 benzyl bromide 
• 73-24-5 7H-purin-6-ylamine 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 50-01-1 guanidine hydrochloride 
• 111267-84-6 1-benzyl-4-cyano-5-<(methoxymethylene)amino>imidazole 
• 206559-19-5 4-benzyl (1,2-dibromo-2-methyl)butyl ether 

Downstream Products

• 83135-11-9 9-benzyl-6-(4-pyridyl)purine 
• 83135-10-8 9-benzyl-6-(2-pyridyl)purine 
• 83135-12-0 9-benzyl-6-(5'-nitro-2'-pyridyl)-9H-purine 1'-oxide 
• 14013-11-7 9-benzylhypoxanthine 
• 83135-09-5 9-benzyl-6-(3-pyridyl)purine 
• 83135-06-2 9-benzyl-6-purine 
• 83135-07-3 9-benzyl-purine 
• 123367-60-2 2-[(9-Benzyl-9H-purin-6-ylamino)-methylene]-indan-1,3-dione 
• 123367-59-9 2-[(9-Benzyl-9H-purin-6-ylamino)-methylene]-5,5-dimethyl-cyclohexane-1,3-dione 
• 83135-05-1 9-benzyl-6-(4-methoxyphenyl)-9H-purine 
• 83135-04-0 9-benzyl-6-(3-methoxyphenyl)-9H-purine 
• 96435-68-6 9-benzyl-1-methyladenine hydroiodide 
• 83135-02-8 9-benzyl-6-phenyl-9H-purine 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 

Relevant academic research and scientific papers

Microwave assisted synthesis and biological activities of 9-boronobenzyladenine derivatives

Microwave enhanced syntheses of 9-boronobenzyladenine derivatives by the reaction of adenine with the corresponding bromomethylphenylboric acid were reported. Microwave irradiation reduced the overnight reaction time of conventional thermal methods to 10

Probing structural consequences of N9-alkylation in silver-adenine frameworks

This communication explores the effect of varying substituent bulk at the N9 position of the adenine moiety and its effect in dictating the structural aspects of silver-adenine frameworks. While adenine alone or 9-benzyl substituted ligand afforded mono a

9-Hydroxymethylcyclopropylidenemethylenyladenine: The design, facile synthesis, isomer separation and Anti-HIV-1 activities

9-Hydroxymethylcyclopropylidenemethylenyladenine was designed based on the analysis of the structure-activity relationship and synthesized by coupling reaction of a vicinal dibromocyclopropane derivative with adenine. The cis/trans isomers and an enantiom

Solvent-directed Regioselective Benzylation of Adenine: Characterization of N9-benzyladenine and N3-benzyladenine

The preferred sites for the benzylation of adenine under basic conditions were proven to be the N9 and N3 positions. Formation of the N9-benzyladenine product is favored in polar aprotic solvents, such as DMSO, whereas the proportion of N3-benzyladenine f

Lead optimization and biological evaluation of fragment-based cN-II inhibitors

The development of cytosolic 5′-nucleotidase II (cN-II) inhibitors is essential to validate cN-II as a potential target for the reversion of resistance to cytotoxic nucleoside analogues. We previously reported a fragment-based approach combined with molecular modelling, herein, the selected hit-fragments were used again in another computational approach based on the Ilib-diverse (a software enabling to build virtual molecule libraries through fragment based de novo design) program to generate a focused library of potential inhibitors. A molecular scaffold related to a previously identified compound was selected and led to a novel series of compounds. Ten out of nineteen derivatives showed 50–75% inhibition on the purified recombinant protein at 200 μM and among them three derivatives (12, 13 and 18) exhibited Ki in the sub-millimolar range (0.84, 2.4 and 0.58 mM, respectively). Despite their only modest potency, the cN-II inhibitors showed synergistic effects when used in combination with cytotoxic purine nucleoside analogues on cancer cells. Therefore, these derivatives represent a family of non-nucleos(t)idic cN-II inhibitors with potential usefulness to overcome cancer drug resistance especially in hematological malignancies in which cN-II activity has been described as an important parameter.

C-H amination of purine derivatives via radical oxidative coupling

An oxidative coupling reaction between purines and alkyl ethers/benzyl compounds was developed to synthesize a series of N9 alkylated purine derivatives using n-Bu4NI as a catalyst and t-BuOOH as an oxidant. This protocol uses commercially available, inexpensive catalysts and oxidants and has a wide range of substrates with a simple operation.

A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo

Cystic fibrosis transmembrane conductance regulator (CFTR) is the main chloride channel present in the apical membrane of epithelial cells and the F508 deletion (F508del-CFTR) in the CF gene is the most common cystic fibrosis-causing mutation. In the sear

8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide

2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified.

Synthetic strategies to 9-substituted 8-oxoadenines

Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Copper-mediated N-arylation in the synthesis of aryladenines

A series of N3 and N9 aryladenines was prepared by arylation of 8-bromoadenine under modified Chan-Lam-Evans coupling conditions followed by reductive debromination with hydrogen on palladium. Conditions of arylation were optimised to maximise the yield o