140914-90-5

Upstream product

• 84500-33-4 2',3',5'-tri-O-acetyl-5-iodouridine 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 69075-42-9 5-ethynyluridine 

Relevant academic research and scientific papers

Water gelation abilities of alkylbenzyltriazole-appended 2′-deoxyribonucleoside and ribonucleoside

Effective hydrogelators based on alkylbenzyltriazole-appended 2′-deoxyribonucleioside and ribonucleoside nucleobase-modified uridine were prepared and the dependence of gelation properties on the nature of single hydroxyl group was investigated. The nucleosides were synthesized by modifying the position of the uracin base with alkylbenzyltriazole units. The small molecular-based gelators of organic and aqueous solvents were prepared from amino acids, bis-ureas, sugars, nucleic acid, and steroids. It was found that the balance between the hydrophilic and hydrophobic characteristics and the nature of the gelators' interactions proved to be an important factors for the small molecular hydrogelators. It was also found that the uridine-based hydrogelators exhibited gelation behavior different to that of corresponding 2-deoxyuridine based systems. The results show that they possess relatively higher minimum gelation concentrations (MGC).

Fluorescent nucleoside derivatives as a tool for the detection of concentrative nucleoside transporter activity using confocal microscopy and flow cytometry

The abundance and function of transporter proteins at the plasma membrane are likely to be crucial in drug responsiveness. Functional detection of human concentrative nucleoside transporters (hCNTs) is of interest for predicting drug sensitivity because of their ability to transport most nucleoside-derived drugs. In the present study, two fluorescent nucleoside analogues, uridine-furan and etheno-cytidine, were evaluated as tools to study in vivo nucleoside transporter-related functions. These two molecules showed high affinity interactions with hCNT1 and hCNT3 and were shown to be substrates of both transporters. Both fluorescence microscopy and flow cytometry experiments showed that uridine-furan uptake was better suited for distinguishing cells that express hCNT1 or hCNT3. These data highlight the usefulness of fluorescent nucleoside derivatives, as long as they fulfill the requirements of confocal microscopy and flow cytometry, for in vivo analysis of hCNT-related function.

Stereoselective Synthesis of Highly Functionalized Arabinosyl Nucleosides through Application of an N-Nitro Protecting Group

2′-Deoxy-2′,5-disubstituted arabinosyl uridine derivatives bearing a halogen (Cl, Br or I) at C2′ and an ethynyl group at C5 have been synthesized in 6 steps from 2′,3′,5′-tri-O-acetyl-5-iodo-uridine in overall yields of 61% (compound 3, Cl), 47% (compound 4, Br), and 19% (compound 5, I). Stabilization of a 2′-O-triflyl leaving group intermediate to overcome spontaneous intramolecular 2,2′-anhydro uridine formation was pivotal to the synthesis. Specifically, to favor SN2 reaction with a halogen nucleophile over intramolecular cyclization, the nucleophilicity of O-2 oxygen was reduced by incorporation of an adjacent electron withdrawing nitro substituent at N-3. The introduction of the 3-N-nitro group proceeded rapidly (nitronium trifluoroacetate, 1 min) and in quantitative yield. A one-pot method to remove the 3-N-nitro group by reductive nitration (zinc metal in acetic acid, 5 min) and the silyl protecting groups of the alkyne and 3′,5′ hydroxyls (fluoride reagent, 16 h) was established as the final synthetic step. This application of the 3-N-nitro protecting group addresses the significant shortfalls of the conventional approach to synthesis of 2′ modified nucleosides, wherein condensation of a 2′ modified sugar fragment with a pyrimidine base provides poor stereocontrol of N-glycosylation, low yields and incompatibility with 2′ iodo sugars.

A chemo-enzymatic approach to specifically click-modified RNA

The growing interest in single-molecule analysis of RNA calls for programmable enzymatic labeling strategies beyond the horizon of solid-phase synthesized RNAs. Herein we describe an easy and versatile chemo-enzymatic approach to label RNA at its termini or defined internal positions via click-chemistry.

Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin- 2(3H)-one base and nucleoside derivatives

Derivatives of the 2′-deoxynucleoside of furo[2,3-d]pyrimidin-2(3H)- one with long-chain alkyl (or 4-alkylphenyl) substituents at C6 exhibit remarkable anti-VZV (varicella-zoster virus) potency and selectivity, and analogous 2′,3′-dideoxynucleoside derivatives show anti-HCMV (human cytomegalovirus) activity. We now report a synthetic approach that enables the preparation of long-chain 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-ones in which the rodlike acetylene spacer replaces the 4-substituted-phenyl ring at C6. Analogues with methyl, β-D-ribofuranosyl, β-D-arabinofuranosyl, and 2-deoxy-β-D-erythro-pentofuranosyl substituents at N3 have been prepared. Long-chain derivatives at C6 in the 2′-deoxynucleoside series showed virus-encoded nucleoside kinase-sensitive anti-VZV activity. Surprisingly, 3-methyl-6-(octyn-1-yl)furo[2,3-d]-pyrimidin-2(3H)-one (prepared as a negative anti-VZV test control) exhibited anti-HCMV activity, which supports the possibility of development of non-nucleoside anti-HCMV agents originating from uncomplicated derivatives of such bicyclic ring systems.

Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity

In this article, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleosides in the 2′-deoxy, 3′-deoxy- and ribosyl series, and we discuss their in vitro anti-HIV and anti-HCV activities and cellular toxicitites. As a result, on the basis of their selectivity index (SI) obtained with the HCV replicon system, but also on their cytotoxicity on peripheral blood mononuclear, CEM and VERO cell lines, the best compounds were the 5-bromoethynyluridine (SI = 3.2) and the 5-(1-chloro-2-iodo) vinyluridine (SI > 2.8).

Design, Synthesis, and Self-Assembly of "Artificial Dinucleotide Duplexes"

The synthesis of the A-U and G-C functionalized systems 1, 2, 3, and 4 has been accomplished using palladium-mediated cross-coupling reactions. These systems undergo self-association in nonpolar solvents such as CDCl3 as judged from FABMS and NMR spectroscopic analyses.