99394-52-2

Basic information

• Product Name: (E)-5-(2-CARBOXYVINYL)URIDINE
• Synonyms: (E)-5-(2-CARBOXYVINYL)URIDINE
• CAS NO: 99394-52-2
• Molecular Formula: C12H14N2O8
• Molecular Weight: 314.25
• Mol File: 99394-52-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-5-(2-CARBOXYVINYL)URIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-(2-CARBOXYVINYL)URIDINE(99394-52-2)
• EPA Substance Registry System: (E)-5-(2-CARBOXYVINYL)URIDINE(99394-52-2)

Safety Data

• Hazardous Substances Data: 99394-52-2(Hazardous Substances Data)

Usage

Description

(E)-5-(2-CARBOXYVINYL)URIDINE is a chemical compound that serves as an intermediate in the synthesis of sulfur-containing uridine anti-cancer compounds, specifically 4-thioxo-5-(2-halovinyl)uridine. It plays a crucial role in the development of potential cancer therapeutics.

Uses

Used in Pharmaceutical Industry:
(E)-5-(2-CARBOXYVINYL)URIDINE is used as a key intermediate in the synthesis of 4-thioxo-5-(2-halovinyl)uridine, a sulfur-containing uridine anti-cancer compound. (E)-5-(2-CARBOXYVINYL)URIDINE holds promise in the development of novel cancer treatments due to its potential to target and inhibit cancer cell growth and proliferation.

Upstream product

• 58931-19-4 methyl 3-(5-uridinyl)propenoate 
• 58-96-8 uridine 
• 1024-99-3 5-iodouridine 
• 123881-85-6 (E)-5-<2-(ethoxycarbonyl)vinyl>uridine 

Downstream Products

• 123881-97-0 5-(1-methoxy-2-iodoethyl)uridine 
• 123881-91-4 5-(1-hydroxy-2-iodoethyl)uridine 
• 86391-68-6 (E)-5-(2-bromovinyl)uridine 
• 114494-92-7 5-(1,2-dibromo-2-succinimidoethyl)uridine 

Relevant articles and documents

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.

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.