Refernces
10.1021/jo962204x
This research study on the synthesis and conformational analysis of cyclohexane nucleosides, specifically focusing on 3-hydroxy-4-(hydroxymethyl)-1-cyclohexanyl purines and pyrimidines. The purpose of the study was to understand the correlation between the antiviral activity of these compounds and their conformational structure. The researchers synthesized the nucleosides using various nucleobases and ethyl 1,3-cyclohexadiene-1-carboxylate through a conjugated addition reaction and hydroboration of the cyclohexenyl precursor. Key chemicals used in the synthesis process included adenine, 2-amino-6-chloropurine, thymine, uracil, cytosine, and various protecting groups like monomethoxytrityl and trityl groups, as well as reagents such as DBU, TFA, and BH3-THF complex. The lack of antiviral activity observed in the synthesized compounds was linked to their conformation, which was deduced from NMR and X-ray analysis. The study concluded that the replacement of the ring oxygen with a methylene group in carbocyclic nucleosides led to a change in the preferred conformation of the nucleoside base from axial to equatorial, which might explain the loss of antiviral activity compared to anhydrohexitol nucleosides.
10.1016/j.tetlet.2009.02.218
The research focuses on the green synthesis of diastereoselective Mannich products using adenine as an aminocatalyst in an aqueous medium of ethanol and water, with hydrogen peroxide as an additive. The purpose of this study was to develop an environmentally benign protocol for the synthesis of β-amino carbonyl compounds, which are important precursors in pharmaceutical and natural product synthesis. The researchers concluded that the use of adenine as a catalyst in this three-component Mannich type reaction led to good yields and improved diastereoselectivity, with the added benefit of not requiring column chromatography for the purification of most compounds, thus overcoming the issue of epimerisation often faced during purification.
10.1021/jm00170a005
The research investigates purine derivatives and analogues as competitive inhibitors of human erythrocyte membrane phosphatidylinositol 4-kinase, with the aim of finding a potent, cell-penetrating inhibitor. The study explores the structural requirements for binding to the ATP site of PI 4-kinase and optimizes inhibitory potency. Key chemicals involved include various purine derivatives such as adenine, 6-substituted purines, 8-substituted adenines, and 9-substituted adenines. The most potent inhibitor synthesized was 9-cyclohexyladenine, with an apparent Ki value of 3.7 pM. Other chemicals like benzoic acid, polyphosphoric acid, and formamide were used in the synthesis of these compounds. The research also involved the use of ATP as the substrate in enzyme assays to determine the inhibitory activities of the synthesized compounds.
10.3987/R-1986-09-2449
The research aimed to develop a new synthetic route to 2-deuterioadenines, which are isotopically labeled adenine derivatives substituted or unsubstituted at the 9-position. These compounds are crucial for biochemical, mechanistic, and spectroscopic studies due to their stability against isotopic exchange. The study successfully synthesized 9-alkyl-2-deuterioadenines (VIII) from 9-substituted adenines (Ib-f) through cyclization of monocyclic intermediates (VIb-e) with formic acid-d2 or 1-(formyl-d)-2(1H)-pyridone. Key chemicals used in the process included formic acid-d2, 1-(formyl-d)-2(1H)-pyridone, Amberlite IRA-402 (OH-), and various 9-substituted adenines. The conclusions highlighted the development of a general and unambiguous synthetic route to 9-substituted 2-deuterioadenines of high isotopic purity, which are expected to be valuable starting materials for syntheses of various adenine structures required for biochemical and spectroscopic investigations.
10.1016/S0960-894X(01)00110-X
The research focuses on the synthesis and hybridization properties of a 9-mer adenine derivative of α-L-LNA (α-L-ribo configured locked nucleic acid), which is a type of nucleic acid mimic designed to have superior properties such as increased stability towards nucleolytic degradation and enhanced binding affinity and specificity towards complementary nucleic acid targets. The study successfully developed a synthetic route for the first α-L-LNA purine monomer, involving the synthesis of a bicyclic adenine nucleoside through a condensation reaction between l-threo-pentofuranose derivative and 6-N-benzoyladenine, followed by C20-epimerization and cyclization. The synthesized α-L-LNA monomers were then incorporated into a 9-mer oligonucleotide, which demonstrated high-affinity hybridization with complementary DNA, RNA, LNA, and α-L-LNA target sequences. The chemicals used in the process included 6-N-benzoyladenine, SnCl4, TMS-triflate, N,O-bis(trimethylsilyl)acetamide, mesyl chloride, sodium hydride, and various other reagents for protection, deprotection, and purification steps. The conclusions of the research were that the α-L-LNA monomers, particularly the adenine derivatives, significantly enhance the affinity of the resulting oligonucleotides for their complementary sequences, and that α-L-LNA:α-L-LNA and α-L-LNA:LNA duplexes form exceptionally stable structures, comparable to LNA:LNA duplexes.
10.1016/S0040-4020(01)89811-2
This study presents an improved method for the synthesis of (+)-carbocyclic 2'-deoxyadenosine, a nucleoside analog with potential antiviral properties, starting from the bicyclic lactone diol (+)-1. The key steps involve the sequential iodide decarboxylation of the carboxylic acid side chain derived from the lactone moiety of (+)-1 using iodobenzene diacetate (IBDA) and a hypervalent iodine species. The tetrahydropyranyl (THP) group was used for protection, replacing the secondary mesyloxy functionality with an azide anion, while a complete inversion of the configuration was performed. The heterocyclic moiety (adenine) was constructed by a modified literature method involving the reduction of NO2 to NH2 groups with SnCl2. The study also reports an unexpected formation of a disubstituted 2-oxabicyclo[2.2.1]heptane skeleton formed via a hypervalent iodine species derived from the intermediate. The overall yield and purity of the final product were improved, highlighting the efficiency of the synthetic route and the importance of the reagents and conditions used.
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