10.1016/j.tet.2010.12.040
The research focuses on the optimized microwave-assisted decomposition of N,N-dimethylformamide (DMF) and its application in amination reactions, particularly in purine chemistry. The study aimed to develop a method for dehalogenative amination (nucleophilic aromatic substitution, SNAr) using the microwave-assisted decomposition of formamides to modify purine derivatives, which are compounds of pharmaceutical interest. The experiments involved the optimization of reaction conditions such as temperature, solvent effect, and the influence of additives like acids, bases, and salts on the decomposition of DMF. Various formamides were used to demonstrate the methodology's applicability in different amination reactions. The analyses included monitoring the decomposition of DMF through pressure changes in a sealed vessel, evaluating the effect of different solvents and additives on the decomposition rate, and conducting amination reactions on various 6-chloropurine derivatives. The products were characterized using techniques such as TLC, NMR, mass spectrometry, and elemental analysis, with yields and reaction conditions being the primary outcomes measured.
10.1016/j.bmc.2009.01.041
The research focuses on the synthesis, characterization, and biological activity of 33 ring-substituted 6-benzylamino-9-tetrahydropyran-2-ylpurine (THPP) and 9-tetrahydrofuran-2-ylpurine (THFP) derivatives, aiming to enhance the specific biological functions of cytokinins used in plant micropropagation. The derivatives were prepared by condensing 6-chloropurine with 3,4-dihydro-2H-pyran or 2,3-dihydrofuran, followed by condensation with corresponding benzylamines. The compounds were characterized using elemental analyses, TLC, HPLC, melting point determinations, CI+ MS, and 1H NMR spectroscopy. The cytokinin activity was assessed through three bioassays: tobacco callus, wheat leaf senescence, and Amaranthus bioassay. Additionally, the susceptibility to enzyme degradation by cytokinin oxidase/dehydrogenase was studied, and the cytotoxicity against human cell lines was evaluated. The stability of selected compounds was also assessed at various pH levels using HPLC.
10.1002/jhet.5570280444
The research focused on the synthesis and evaluation of a series of 6-substituted-9-(3-formamidobenzyl)purines for their benzodiazepine receptor (BZR) binding activity. The purpose was to explore the effects of structural changes on BZR binding activity and in vivo Geller-Seifter Conflict activity. The study concluded that while several of these compounds bound to the BZR with potency comparable to benzodiazepines, none exhibited significant in vivo activity in the Geller-Seifter Conflict test, suggesting they may act as antagonists rather than agonists. Key chemicals used in the synthesis process included various amines, alcohols, and nucleophilic reagents for the substitution reactions, as well as reagents like sodium hydroxide, sodium azide, formic acid, and catalytic hydrogenation for specific transformations. The target compounds were derived from 6-chloropurine and 9-(3-formamidobenzyl)-9H-purine, with substitutions at the 6-position leading to a range of structurally diverse purines.