86163-17-9

Usage

Uses

Used in Antiviral Applications:
(E)-5-(2-Carbomethoxyvinyl)-2'-deoxyuridine is used as an antiviral agent for its ability to inhibit viral replication and reduce the severity of viral infections. Its unique structure allows it to target specific viral enzymes, making it a promising candidate for the development of new antiviral therapies.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (E)-5-(2-Carbomethoxyvinyl)-2'-deoxyuridine is used as a key intermediate in the synthesis of antiviral drugs. Its unique chemical properties enable the development of innovative drug formulations with improved efficacy and safety profiles.
Used in Research and Development:
(E)-5-(2-Carbomethoxyvinyl)-2'-deoxyuridine is also utilized in research and development for studying the mechanisms of viral infections and the development of resistance to antiviral drugs. Its use in laboratory settings contributes to a better understanding of viral diseases and the discovery of new treatment options.

Upstream product

• 951-78-0 2'-deoxyuridine 
• 292638-85-8 acrylic acid methyl ester 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 611-53-0 5-Iodo-2'-deoxycytidine 
• 65505-76-2 5-chloromercuri-2'-deoxyuridine 
• 76772-94-6 5-Iodo-4-trimethylsilanyloxy-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 

Downstream Products

• 74131-06-9 (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid 
• 840506-24-3 (E)-5-(2-bromovinyl)-2’-deoxyuridine-5’-(1-phenylmethoxy-L-phenylalanyl)phosphate 
• 1056651-21-8 5'-O-(4,4'-dimethoxytrityl)-5-(2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine 
• 1056651-22-9 5'-O-(4,4'-dimethoxytrityl)-5-(2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine 3'-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite 

Relevant academic research and scientific papers

Nucleic acid probe, method for designing nucleic acid probe, and method for detecting target sequence

The present invention provides a nucleic acid probe that can achieve high detection sensitivity and high specificity in mutation detection, mismatch detection, etc. by the PCR method, a method for designing such a nucleic acid probe, and a method for detecting a target sequence. The nucleic acid probe includes a nucleic acid molecule, and the nucleic acid molecule includes a plurality of fluorescent dye moieties that exhibit an excitonic effect. At least two of the fluorescent dye moieties that exhibit an excitonic effect are bound to the same base or two adjacent bases in the nucleic acid molecule with each fluorescent dye moiety being bound via a linker (a linking atom or a linking atomic group). The extension-side end of the nucleic acid molecule is chemically modified, thereby preventing an extension reaction of the nucleic acid molecule.

ProTides of BVdU as potential anticancer agents upon efficient intracellular delivery of their activated metabolites

Nucleosides represent a major chemotherapeutic class for treating cancer, however their limitations in terms of cellular uptake, nucleoside kinase-mediated activation and catabolism are well-documented. The monophosphate pro-nucleotides known as ProTides represents a powerful strategy for bypassing the dependence on active transport and nucleoside kinase-mediated activation. Herein, we report the structural tuning of BVdU ProTides. Forty six phosphoramidates were prepared and biologically evaluated against three different cancer cell lines; murine leukemia (L1210), human CD4+T-lymphocyte (CEM) and human cervical carcinoma (HeLa). Twenty-fold potency enhancement compared to BVdU was achieved against L1210 cells. Interestingly, a number of ProTides showed low micromolar activity against CEM and HeLa cells compared to the inactive parent BVdU. The ProTides showed poor, if any measurable toxicity to non-tumourigenic human lung fibroblast cell cultures. Separation of four pairs of the diastereoisomeric mixtures and comparison of their spectral properties, biological activities and enzymatic activation rate is reported.

Novel water-soluble phosphatriazenes: Versatile ligands for Suzuki-Miyaura, Sonogashira and Heck reactions of nucleosides

Two new water-soluble phosphatriazene ligands have been synthesized as versatile ligands for complexation reactions with Pd(OAc)2 and utilized for catalyzing column-free Suzuki-Miyaura cross-coupling of various purine and pyrimidine halonucleosides in water. The water-solubility of the catalytic system simplified the isolation of the cross-coupled products to mere filtration, while the catalytically active solution in the filtrate was recycled eight times. A novel copper-free Sonogashira coupling protocol for the nucleosides has also been established via a one-pot synthesis of FV-100, a nucleoside-based drug in phase 3 clinical trials for herpes zoster or shingles treatment. Application of the Heck reaction was demonstrated by the synthesis of another antiviral drug: BVDU.

Pd-imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction

Pd-imidate complexes have been employed as efficient catalysts for the Heck alkenylation of unprotected 5-iodo-2′-deoxyuridine in acetonitrile. The protocol was also shown to work well for the unprotected 5-iodo-2′-deoxycytidine. A highly efficient scale-up synthesis of the HSV-1 inhibitor Brivudine (BVDU) is also accomplished in an overall yield of 72% over 3-steps. The catalyst also showed recyclability for 3 consecutive runs.

COMPOUND, NUCLEIC ACID, METHOD FOR PRODUCING NUCLEIC ACID, AND KIT FOR PRODUCING NUCLEIC ACID

A compound is represented by the following formula (1), (2), or (3) (where, in the above formulae (1), (2), and (3), Z11 and Z12 independently have a fluorescent property and are an uncharged atomic group exhibiting an exciton effect).

Synthesis, cytotoxicity, and insight into the mode of action of Re(CO) 3 thymidine complexes

Nucleoside analogues are extensively used in the treatment of cancer and viral diseases. The antiproliferative properties of organorhenium(I) complexes, however, have been scarcely explored to date. Herein we present the syntheses, characterization, and in vitro evaluation of ReI(CO)3 core complexes of thymidine and uridine. For the binding of the Re I(CO)3 core, a tridentate dipicolylamine metal chelate was introduced at positions C5′, C2′, N3, and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying the rhenium moiety at position C5′ or N3 (IC50=124-160 μm). No toxicity was observed for complexes modified at C2′ or C5. Complex 53, with a dodecylene spacer at C5′, exhibits remarkable toxicity and is more potent than cisplatin, with an IC50 value of 6.0 μm. To the best of our knowledge, this is the first report of the antiproliferative properties of [M(CO)3]+1-nucleoside conjugates. In competitive inhibition experiments with A549 cell lysates and purified recombinant human thymidine kinase 1 (hTK-1), enzyme inhibition was observed for complexes modified at either N3 or C5′, but our results suggest that the toxicity cannot be attributed solely to interaction with hTK-1.

A light-controlled reversible DNA photoligation via carbazole-tethered 5-carboxyvinyluracil

We describe a light-controlled template-directed reversible DNA photoligation via carbazole-tethered 5-carboxyvinyluracil. Carbazole-tethered 5-carboxyvinyl-2'-deoxyuridine-containing oligodeoxynucleotide (ODN) can be ligated by irradiation at 366 nm in the presence of template ODN, and the ligated ODN can be split by irradiation at 366 nm in the absence of template ODN.

A versatile toolbox for variable DNA functionalization at high density

To broaden the applicability of chemically modified DNAs in nano- and biotechnology, material science, sensor development, and molecular recognition, strategies are required for introducing a large variety of different modifications into the same nucleic acid sequence at once. Here, we investigate the scope and limits for obtaining functionalized dsDNA by primer extension and PCR, using a broad variety of chemically modified deoxynucleotide triphosphates (dNTPs), DNA polymerases, and templates. All natural nucleobases in each strand were substituted with up to four different base-modified analogues. We studied the sequence dependence of enzymatic amplification to yield high-density functionalized DNA (fDNA) from modified dNTPs, and of fDNA templates, and found that GC-rich sequences are amplified with decreased efficiency as compared to AT-rich ones. There is also a strong dependence on the polymerase used. While family A polymerases generally performed poorly on "demanding" templates containing consecutive stretches of a particular base, family B polymerases were better suited for this purpose, in particular Pwo and Vent (exo-) DNA polymerase. A systematic analysis of fDNAs modified at increasing densities by CD spectroscopy revealed that single modified bases do not alter the overall B-type DNA structure, regardless of their chemical nature. A density of three modified bases induces conformational changes in the double helix, reflected by an inversion of the CD spectra. Our study provides a basis for establishing a generally applicable toolbox of enzymes, templates, and monomers for generating high-density functionalized DNAs for a broad range of applications.

CHEMICAL COMPOUNDS

Phosphoramidate derivatives of nucleotides and their use in the treatment of cancer are described. The base moieties of, for example, each of deoxyuridine, cytarabine, gemcitabine and citidine may be substituted at the 5-position. The phosphoramidate moiety has attached to the P atom an aryl-O moiety and an α-amino acid moiety. The α-amino acid moiety may correspond to or be derived from either a naturally occurring or a non-naturally occurring amino acid.

Synthesis of 5-tethered carborane-containing pyrimidine nucleosides as potential agents for DNA incorporation

Several 5-substituted-2'-deoxyuridines have been prepared in which the carborane moiety is attached at the terminus of a flexible hydrocarbon chain containing an ester linkage. These boron moieties as the B-10 enriched compounds have potentially for use in the treatment of cancer by means of boron neutron capture therapy. A convenient synthetic route, in high yield, has been developed for the preparation of these 5-tethered carborane- containing pyrimidine nucleosides.