76756-28-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione is used as a pharmaceutical agent for the treatment of various genetic and viral diseases. Its role in DNA synthesis and replication makes it a key component in the development of therapeutic strategies for these conditions.
Used in Cancer Therapy:
In the field of oncology, 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione is utilized for its potential applications in cancer treatment. Its involvement in DNA synthesis and cell division processes makes it a candidate for targeting rapidly dividing cancer cells.
Used in Antiviral Treatments:
1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione is also used in antiviral treatments, where its role in DNA synthesis can be leveraged to inhibit viral replication and reduce the spread of viral infections.
Used in Laboratory Research:
In the scientific community, 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione is employed in laboratory experiments to study DNA synthesis, cell division, and the mechanisms of genetic and viral diseases. Its presence in all living organisms makes it an essential tool for understanding the fundamental processes of life.

Upstream product

• 591-50-4 iodobenzene 
• 65505-76-2 C⁵-chloromercuri-2'-deoxyuridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 934-56-5 trimethyl(phenyl)stannane 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 951-78-0 2'-deoxyuridine 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 71-43-2 benzene 
• 76772-94-6 5-Iodo-4-trimethylsilanyloxy-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 
• 137100-79-9 3'-O,5'-O,N³-tritoluoyl-5-iodo-2'-deoxyuridine 
• 78824-31-4 di-O-trimethylsilyl-5-iodo-2'-deoxyuridine 

Downstream Products

• 1574218-93-1 5′-(4,4′-dimethoxytrityloxymethyl)-5-phenyl-2′-deoxyuridine 
• 1574218-98-6 3′-O-(P-(2-cyanoethoxy)-N,N′-diisopropylaminophosphinyl)-5′-(4,4′-dimethoxytrityl)-5-phenyl-2′-deoxyuridine 
• 76756-31-5 C₁₅H₁₅N₂O₈P^(2-) 

Relevant academic research and scientific papers

Supported synthesis and functionnalization of 2″-deoxyuridine by Suzuki-Miyaura cross-coupling

The synthesis and modification of 2′-deoxyuridine has been realized under Suzuki-Miyaura palladium-catalyzed cross-coupling conditions. Using Pd(PPh3)4 and Na2CO3, 5-iodo-2′-deoxyuridine bound to solid support is coupled with various boronic acids to give

PALLADIUM(0) CATALYZED COUPLING REACTIONS IN THE SYNTHESIS OF 5-ARYLPYRIMIDINE NUCLEOSIDES

The palladium(0) catalyzed coupling reaction of arylioides and 3',5'-di-O-acetyl-5-chloromercuri-2'-deoxyuridine (1) gave 5-aryl substituted 2'-deoxyuridines.Optimum yields were obtained in diglyme at 120 deg C for 3 hours.

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

Imine-Palladacycles as Phosphine-Free Precatalysts for Low-Temperature Suzuki-Miyaura Synthesis of Nucleoside Analogues in Aqueous Media

The synthesis and characterization of new water-soluble dinuclear palladacycles of the general formula [{Pd(R-C^N-SO3Na)(μ-AcO)}2] (R = H (1), OMe (2), Cl (3)) incorporating an ortho-metalated sodium 4-(N-benzylideneamino)benzenesulfonate moiety is reported. These complexes have been revealed to be excellent phosphine-free catalysts for the synthesis of functionalized nucleoside analogues involving a low-temperature Suzuki-Miyaura coupling of 5-iodo-2′-deoxyuridine with different arylboronic acids in neat water. The potential of 1-3 as synthetic precursors was also tested, and bridging acetates were cleaved by reaction with neutral PPh3, yielding the corresponding mononuclear derivatives [Pd(R-C^N-SO3Na)(AcO)(PPh3)] (R = H (4), MeO (5), Cl (6)). Analytical and spectroscopic techniques confirmed the proposed formulas and reactivities reported for complexes 1-6. Structural characterization by X-ray diffraction of single crystals grown from samples of 4 and 6 produced the unexpected but valuable crystallization-mediated compounds 4cm and 6cm that also supported the results presented here.

COMPOUNDS, COMPOSITIONS, AND METHODS FOR THE TREATMENT OF DISEASE

This invention relates to compounds and compositions for the induction of expression of a pattern recognition receptor (e.g., STING) and methods of use thereof.

COMPOUNDS, COMPOSITIONS, AND METHODS FOR THE TREATMENT OF DISEASE

This invention relates to compounds and compositions for the induction of expression of a pattern recognition receptor (e.g., STING) and methods of use thereof.

High-affinity RNA targeting by oligonucleotides displaying aromatic stacking and amino groups in the major groove. Comparison of triazoles and phenyl substituents

Three 5-modified 2′-deoxyuridine nucleosides were synthesized and incorporated into oligonucleotides and compared with the previously published 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridine monomer W. The introduction of an aminomethyl group on the phenyl group led to monomer X, which was found to thermally stabilize a 9-mer DNA:RNA duplex, presumably through the partial neutralization of the negative charge of the backbone. By also taking advantage of the stacking interactions in the major groove of two or more of the monomer X, an extremely high thermal stability was obtained. A regioisomer of the phenyltriazole substituent, that is the 5-(4-phenyl-1,2,3-triazol-1-yl)- 2′-deoxyuridine monomer Y, was found to destabilize the DNA:RNA duplex significantly, but stacking in the major groove compensated for this when two to four monomers were incorporated consecutively. Finally, the 5-phenyl-2′-deoxyuridine monomer Z was incorporated for comparison, and it was found to give a more neutral influence on duplex stability indicating less efficient stacking interactions. The duplexes were investigated by CD spectroscopy and MD simulations.

New water soluble Pd-imidate complexes as highly efficient catalysts for the synthesis of C5-arylated pyrimidine nucleosides

The direct reactions between the precursors trans-[Pd(imidate) 2(SMe2)2] and 1,3,5-triaza-7-phosphaadamantane (PTA) yield new water-soluble palladium(ii) complexes trans-[Pd(imidate) 2(PTA)2](imidate

New, efficient approach for the ligand-free Suzuki-Miyaura reaction of 5-iodo-2′-deoxyuridine in water

A series of 5-aryl-2′-deoxyuridines was prepared, using ligandless Suzuki-Miyaura cross-coupling reactions in neat water, starting from 5-iodo-2′-deoxyuridine as totally deprotected starting material. This ligand-free process gave good to high isolated yi

Improved microwave-assisted ligand-free Suzuki-Miyaura cross-coupling of 5-iodo-2′-deoxyuridine in pure water

A facile and efficient methodology for direct synthesis of 5-aryl-2′-deoxyuridines was developed through ligand-free Suzuki-Miyaura cross-coupling reactions starting from totally deprotected 5-iodo-2′- deoxyuridine and various boronic acids. Reactions wer