69304-48-9

Usage

Uses

Used in Antiviral Applications:
(E)-5-(2-Iodovinyl)-2-deoxyuridine is used as an antiviral agent for treating herpes simplex virus infections. It functions by disrupting viral DNA replication, thereby inhibiting the growth and spread of the virus.
Used in Cancer Therapy:
In the field of oncology, (E)-5-(2-Iodovinyl)-2-deoxyuridine is used as a therapeutic agent. It has the potential to selectively target cancer cells and inhibit their growth, making it a promising candidate for cancer treatment.
Used in Gene Therapy:
(E)-5-(2-Iodovinyl)-2-deoxyuridine is also being explored for its application in gene therapy. Its ability to interfere with DNA synthesis and replication processes could be harnessed to develop novel treatment strategies for genetic disorders.
Used in Research:
Furthermore, (E)-5-(2-Iodovinyl)-2-deoxyuridine serves as a valuable tool in research settings. It aids in the study of DNA synthesis and replication processes, contributing to a deeper understanding of these fundamental biological mechanisms.

Upstream product

• 69304-50-3 5-[(E)-2-iodoethenyl]-2,4(1H,3H)-pyrimidinedione 
• 37107-81-6 5-vinyluracil 
• 73446-76-1 bis(trimethylsilyl) derivative of (E)-5-(2-iodovinyl)uracil 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 178179-66-3 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-((E)-2-trimethylsilanyl-vinyl)-1H-pyrimidine-2,4-dione 
• 73456-10-7 E-5-(2-iodovinyl)-3',5'-di-O-p-toluoyl-2'-deoxyuridine 
• 57412-59-6 (E)-5-(2-carboxyvinyl)uracil 
• 1195-08-0 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of Some 5-Halogenovinyl Derivatives of Uracil and their Conversion into 2'-Deoxyribonucleosides

Treatment of 5-formyluracil with malonic acid in the presence of piperidine gave (E)-5-(2-carboxyvinyl)uracil which, upon reaction with the appropriate N-halogenosuccinimide, gave (E)-5-(2-bromovinyl)uracil, (E)-5-(2-chlorovinyl)uracil, and (E)-5-(2-iodovinyl)uracil.The last mentioned compound was also obtained by the action of iodine chloride on 5-vinyluracil. 5-(1-Chlorovinyl)uracil upon treatment with bromine gave 5-(2-bromo-1-chlorovinyl)uracil which reacted with sodium methoxide to give 5-bromoethynyluracyl. (E)-5-(2-Bromovinyl)uracil was converted into its trimethylsilyl derivative which was condensed with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride to give the α- and β-anomers of the blocked deoxyribonucleoside.Removal of the p-toluoyl blocking groups with sodium methoxide afforded (E)-5-(2-bromovinyl)-1-(2-deoxy-α-D-erythro-pentofuranosyl)uracil and (E)-5-(2-bromovinyl)-2'-deoxyuridine.A similar series of reactions gave (E)-5-(2-iodovinyl)-2'-deoxyuridine and 5-(2-bromo-1-chlorovinyl)-2'-deoxyuridine. 5-(1-Chlorovinyl)uracil could be condensed similarly with the blocked sugar derivative to give the α- and β-anomers of the blocked deoxyribonucleoside.Attempted removal of the groups with sodium methoxide gave 2'-deoxy-5-ethynyluridine and mild treatment with methanolic ammonia gave the same product and some 2'-deoxy-5-ethynyl-5'-O-(p-toluoyl)uridine. 5-(1-Chlorovinyl)-2'-deoxyuridine was obtained by the addition of HCl to 2'-deoxy-5-ethynyluridine.Aspects of the elimination reactions of 5-(halogenovinyl)uracil derivatives are discussed.

Nucleoside analogue phosphates for topical use

Compositions for topical use in herpes virus infections comprising anti-herpes nucleoside analogue phosphate esters, such as acyclovir monophosphate, acyclovir diphosphate, and acyclovir triphosphate which show increased activity against native strains of herpes virus as well as against resistant strains, particularly thymidine kinase negative strains of virus. Also disclosed are methods for treatment of herpes infections with nucleoside phosphates. Anti-herpes nucleoside analogues phosphate esters include the phosphoramidates and phosphothiorates, as well as polyphosphates comprising C and S bridging atoms.

Synthesis and cellular uptake of 2'-substituted analogues of (e)-5-(2- [125i]iodovinyl)-2'-deoxyuridine in tumor cells transduced with the herpes simplex type-1 thymidine kinase gene. Evaluation as probes for monitoring gene therapy

A useful synthetic methodology was developed to synthesize and radiolabel a series of (E)-5(2-[125I)iodovinyl)uracil nucleoside substrates for herpes simplex virus type-1 thymidine kinase (HSV-1 TK). (E)- 5-(2-[125I]Iodovinyl)-2'-deoxyuridine ([125I]IVDU, 10), (E)-5-(2- [125I]iodovinyl)2'-fluoro-2'-deoxyuridine ([125I]IVFRU, 11), (E)-5-(2- [125I]iodovinyl)-2'-fluoro-2'-deoxyarabinouridine ([125I]IVFAU, 12), and (E)-5-(2-[125I]iodovinyl)arabinouridine ([125I]IVAU, 13) were synthesized in 63-83% radiochemical yield by reaction of the unprotected (E)- 5-(2-(trimethylsilyl)vinyl) precursors (6-9)with [125I]ICl. Cellular uptake of these labeled compounds (1018) was evaluated in vitro. All compounds showed minimal uptake in the KBALB cell line. However, increased uptake was observed for all compounds in KBALB-STK cells which are transduced with a replication incompetent Moloney murine leukemia virus vector encoding the HSV-1 TK gene. The results indicate that uptake of these compounds in KBALB-STK cells is variable and highly dependent on the nature of the sugar 2'-substituent. When a fluoro (12) or a hydroxy (13) substituent is present in the arabinofuranosyl (up) configuration at the 2'-position, there is diminished cellular uptake in KBALB-STK cells relative to hydrogen (10) or fluorine (11) in the ribofuranosyl (down) configuration at the 2'-position. Our results indicate that radiolabeled IVFRU (11) is most promising for further in vivo studies.

2'Deoxy-5-(2-halogenovinyl)-uridines, pharmaceutical compositions and method of use

The novel substance E-5-(2-bromovinyl)-2'-deoxyuridine and its corresponding iodovinyl derivative are gifted with specific antiviral activities towards herpes simplex virus. They may be synthesized by a condensation reaction followed by separation of anomers.