Synthesis and Reactions of 2,6-Diazidopurine Deoxynucleoside

In recent years number of novel 1,2,3-triazolylpurine nucleosides have been synthesized including compounds with biological activity: adenosine receptor antagonists and agonists, anticancer and antiviral agents. In this research synthesis of 2,6-bistriazolyl deoxynucleosides in Cu catalysed 1,3-dipolar azide-alkyne cycloaddition reaction (Click reaction) has been investigated

Purine Deoxyribonucleoside Triazolyl Derivatives: Synthesis and Application

Synthesis of nucleoside analogs is a routine approach in search of fluorescent probes for labeling of nucleic acids or biologically active compounds. In last years our group has reported the synthesis of 2,6-bis-triazolyl ribo- and arabinonucleosides. To continue our previous work, synthesis and properties of deoxyribo- analogs have been investigated

"Click" Approach to the Synthesis of 2,6-Bis(1,2,3-triazolyl)purine Deoxynucleosides

Azide-alkyne 1,3-dipolar cycloaddition reaction (click reaction) has been found to be useful in nucleoside, nucleotide and oligonucleotide chemistry. In last years a number of 1,2,3-triazolylnucleoside derivatives have been synthesized and investigated, leading to discovery of substances with antiviral and anticancer activity, enzyme inhibitors, adenosine receptor agonists and antagonists

Synthesis and Fluorescence Properties of 2-Methylamino-6-triazolylpurine Deoxyribonucleoside

The fluorescent nucleoside isomorphs are tools used for the exploration of structure and interactions of nucleic acids. For instance, they are employed in single-nucleotide polymorphysm assays and for the investigation of interactions between nucleic acids and drugs. Recently, a method for the synthesis of nucleoside analogues possessing fluorescent properties was reported by our group. This approach is used in the present research for the synthesis of a novel compound. Its fluorescent properties have shortly been examined leading to interesting results

A Simple Route to Fluorescent Nucleosides via Purine Bis-triazolyl Derivatives

Environmentally sensitive fluorescent nucleosides are attractive as reporter molecules. Herein we present the results of our research of purine nucleoside 6-amino-2-triazolylderivatives that exhibit fluorescent properties and are readily available from reaction of corresponding 2,6-bis-triazolylpurine nucleosides with amines. The N-nucleophiles suitable for SNAr reaction include even sterically hindered secondary amines, hydrazines, amino acids and thiols. In addition, 2,6-bis-triazolylpurine nucleosides readily produce peptide-nucleoside conjugates. The photophysical properties of synthesized fluorescent nucleosides were investigated. From our research in ribo-, deoxyribo- and arabino- series we concluded that the fluorescence properties of the obtained products are practically unaffected by sugar moiety. On the other hand, the emission spectra and quantum yields sensitively changed according to solvent properties. The solvatochromic properties of newly designed fluorescent nucleosides will be discussed. The fluorescent adenosine analogue N6-methyl-2-(1,2,3-triazol-1-yl)deoxyadenosine (A*) has been incorporated in trinucleotide sequence d(CA*G). Although the quenching of fluorescence was observed due to the presence of other nucleobases, the developed trinucleotide still retain experimentally useful levels of fluorescence

Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C-H Functionalizations

The synthesis of a set of cobalt(III)-complexes equipped with trisubstituted chiral cyclopentadienyl ligands is reported, and their steric and electronic parameters are mapped. The application potential of these complexes for asymmetric C-H functionalizations with 3d-metals is shown by the synthesis of dihydroisoquinolones from N-chlorobenzamides with a broad range of alkenes. The transformation proceeds with excellent enantioselectivities of up to 99.5:0.5 er and high regioselectivities. The observed values outperform the best rhodium(III)-based methods for this reaction type. Moreover, challenging substrates such as alkyl alkenes also react with high regio- and enantioselectivities

Synthesis and Transformations of 2,6-Diazidopurine Deoxynucleoside

In recent years a number of 1,2,3-triazolylnucleoside derivatives have been synthesised and investigated, leading to the discovery of substances with antiviral and anticancer activity, enzyme inhibitors, adenosine receptor agonists and antagonists. The aim of this research is to achieve 2,6-diazidopurine deoxyribonucleoside using deoxyguanosine or 2,6-diazidopurine as the starting material, and to investigate its reactions with terminal alkynes

Novel Fluorescent Deoxyribonucleoside with Promising Fluorescent Properties

The fluorescent nucleoside isomorphs are tools used for the exploration of structure and interactions of nucleic acids. For instance, they are employed in single-nucleotide polymorphysm assays and for the investigation of interactions between nucleic acids and drugs. Recently, a method for the synthesis of nucleoside analogues possessing fluorescent properties was reported by our group. This approach is used in the present research for the synthesis of a novel compound. Its fluorescent properties have shortly been examined leading to interesting results

Synthesis and X-Ray Studies of 2,6-Diazido Purine Deoxyribo-Nucleoside

In recent years various 1,2,3-triazolylpurine nucleosides with anticancer and antiviral activity have been obtained. A number of novel ribo- and arabino-nucleoside bis-triazolyl derivatives have been reported by our research group. Since the synthesis of bis-triazolyl purine deoxyribo- analogues is not known, our first aim was to acquire the key intermediates