58931-19-4

Usage

Uses

Used in Biotechnology Industry:
(E)-5-(2-Carbomethoxyvinyl)uridine is used as a reactant/reagent for the preparation of modified nucleosides, nucleotides, and nucleic acids. These modified molecules are essential for the development of novel therapeutic agents and diagnostic tools, as they can be incorporated into various biological systems to study and manipulate cellular processes.
Used in Pharmaceutical Industry:
(E)-5-(2-Carbomethoxyvinyl)uridine is used as a reactant/reagent for the preparation of human granulocyte-colony stimulating factor (G-CSF)-modified mRNA. This modified mRNA can induce cell proliferation, which has potential applications in the treatment of various diseases and conditions that involve cell growth and regeneration, such as wound healing, tissue repair, and certain types of cancer.

Upstream product

• 1024-99-3 5-iodouridine 
• 292638-85-8 acrylic acid methyl ester 
• 58-96-8 uridine 
• 111582-84-4 1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-4-trimethylsilanyloxy-1H-pyrimidin-2-one 

Downstream Products

• 99394-52-2 (E)-5-(2-carboxyvinyl)uridine 
• 86391-68-6 (E)-5-(2-bromovinyl)uridine 

Relevant academic research and scientific papers

Synthesis and Antiviral Activity of (E)-5-(2-Bromovinyl)uracil and (E)-5-(2-Bromovinyl)uridine

(E)-5-(2-Bromovinyl)uracil (BVU) and (E)-5-(2-bromovinyl)uridine (BVRU) were synthesized starting from 5-formyluracil via (E)-5-(2-carboxyvinyl)uracil or starting from 5-iodouridine via (E)-5-(2-carbomethoxyvinyl)uridine and (E)-5-(2-carboxyvinyl)uridine, respectively.Depending on the choice of the cell system, BVU and BVRU exhibited a marked activity against herpes simplex virus type 1 (HSV-1) in vitro.Although BVU and BVRU were less potent than the reference compound (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU), their antiviral activity spectrum was remarkably similar to that of BVDU.The latter findings suggest that BVU and BVRU are metabolically converted to BVDU or a phosphorylated product thereof.In vivo, BVU protected mice against a lethal disseminated HSV-1 infection.

Sulfur-containing uridine anticancer compound and intermediate and preparation method thereof

The invention relates to a 4-sulfur-5-(2-halogenated vinyl)uridine compound which has the higher sensibility to UVA light and the anticancer activity and an intermediate and a preparation method of the compound. The method comprises the following steps that an iodination reaction is performed, a halogenating reaction is performed, hydroxyl on a sugar ring is protected, oxygen is replaced by sulfur, an O protection group is removed, and then 4-sulfur-5-(2-halogenated vinyl)uridine is obtained. The method has the advantages of being short in reaction time and high in yield and product purity, and the defects that in a traditional synthesis method, time and energy are consumed, and the yield is low are overcome. Beneficial conditions are supplied for further developing sulfur-containing nucleoside drugs.

Bifunctional inhibition of HIV-1 reverse transcriptase: A first step in designing a bifunctional triphosphate

The onset of resistance to approved anti-AIDS drugs by HIV necessitates the search for novel inhibitors of HIV-1 reverse transcriptase (RT). Developing single molecular agents concurrently occupying the nucleoside and nonnucleoside binding sites in RT is an intriguing idea but the proof of concept has so far been elusive. As a first step, we describe molecular modeling to guide focused chemical syntheses of conjugates having nucleoside (d4T) and nonnucleoside (TIBO) moieties tethered by a flexible polyethylene glycol (PEG) linker. A triphosphate of d4T-6PEG-TIBO conjugate was successfully synthesized that is recognized as a substrate by HIV-1 RT and incorporated into a double-stranded DNA.

A Simple Synthesis of 5-(1-Alkenyl)uracil Derivatives by Palladium-Catalyzed Oxidative Coupling of Uracils With Olefins

The oxidative coupling of uracil derivatives 1 with olefins, such as methyl acrylate, acrylonitrile, methyl vinyl ketone, and styrene, using one equivalent of palladium acetate leads to the corresponding 5-(1-alkenyl)uracil derivatives 2.

Photochemical synthesis of 5-alkylpyrimidine nucleosides

5-Alkylpyrimidine nucleosides, bearing different functional groups attached to the newly formed carbon chains at C-5, were synthesized via a photocoupling reaction, 5-(2-Hydroxyethyl)uridine and its derivatives were obtained from the reaction of uridine (U) or 2'deoxyuridine (DU) with 2-iodoethanol.Trimethylsilyl derivatives of 5-iodouridine (IU) and 5-iodo-2'-deoxyuridine (IDU), when treated with methyl acrylate, gave methyl 3-(5-uridinyl)propenoate and methyl 3-(2'-deoxy-5-uridinyl) propenoate, respectively, which, upon catalytic hydrogenation, afforded 5-uridine and its 2-deoxyuridine analogue.IU and IDU also gave 5-(2-cyanoethenyl)uridine and its 2'-deoxyuridine analogue, when treated with acrylonitrile.The latter compounds gave the corresponding 5-(2-cyanoethyl) nucleosides when subjected to catalytic hydrogenation.