119410-95-6

Basic information

• Product Name: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 119410-95-6
• Molecular Formula: C₁₀H₁₂N₂O₅
• Molecular Weight: 240
• Mol File: 119410-95-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 173.5 °C (decomp)
• Appearance: /
• Density: 1.53±0.1 g/cm3(Predicted)
• PKA: 9.29±0.10(Predicted)
• CAS DataBase Reference: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione(119410-95-6)
• EPA Substance Registry System: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione(119410-95-6)

Safety Data

• Hazardous Substances Data: 119410-95-6(Hazardous Substances Data)

Usage

Description

1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione, also known as 2''-Deoxy-2''-methyleneuridine, is a chemical compound with a complex structure derived from the pyrimidine and tetrahydrofuran families. It is an analog of Uridine (U829910) and exhibits a range of biological activities, including antiherpesvirus, antitumor, antiviral, and anticancer properties.

Uses

Used in Antiviral Applications:
1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione is used as an antiviral agent for its antiherpesvirus activity, helping to inhibit the replication and spread of herpesviruses in infected cells.
Used in Anticancer Applications:
In the field of oncology, 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione is used as an anticancer agent, leveraging its antitumor properties to target and suppress the growth of cancer cells.
Used in Pharmaceutical Industry:
1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione is utilized in the pharmaceutical industry as a potential drug candidate due to its diverse therapeutic activities, including antiviral and anticancer effects, making it a promising compound for the development of new medications.

Upstream product

• 79-37-8 oxalyl dichloride 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 58-96-8 uridine 
• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 114262-49-6 1-(2'-C-methyl-β-D-arabinofuranosyl)uracil 
• 84828-97-7 1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 
• 146952-83-2 3',5'-di-O-acetyl-2'-deoxy-2'-methylene-β-D-uridine 
• 134660-24-5 1-((2R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)pyrimidine-2,4 (1H,3H)-dione 
• 102789-14-0 1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-pyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 142688-36-6 2'-deoxy-2'-methylidene-5'-O-trityluridine 
• 146952-84-3 1-((2R,4S,5R)-5-Hydroxymethyl-3-methylene-4-trityloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 148943-50-4 1-(5-O-(tert-Butyldiphenylsilyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)uracil 
• 1610022-30-4 (2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methylene-2-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3-yl ((perfluorobenzoyl)oxy)carbamate 
• 1610022-28-0 1-((2R,4S,5R)-4-hydroxy-3-methylene-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 1496551-72-4 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 1496551-77-9 MK-3682 
• 146952-85-4 O²,3'-anhydro-2'-deoxy-2'-methylidene-5'-O-trityluridine 
• 142688-37-7 Methanesulfonic acid (2R,3S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methylene-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 142688-39-9 (3'R)-2'-deoxy-2'-methylidene-5'-O-trityluridine 
• 142688-44-6 (3'S)-3'-tert-butoxycarbonylamino-2',3'-dideoxy-2'-methylidene-5'-O-tritylcytidine 
• 142688-43-5 (3'S)-3'-tert-butoxycarbonylamino-2',3'-dideoxy-2'-methylidene-5'-O-trityluridine 
• 142688-38-8 (3'R)-3'-O-benzoyl-2'-deoxy-2'-methylidene-5'-O-trityluridine 
• 142688-42-4 2',3'-didehydro-2',3'-dideoxy-2'-phenylselenomethyl-5'-O-trityluridine 

Relevant articles and documents

Novel intramolecular aminohydroxylation toward the syntheses of 2′-amino-2′-ethynyl nucleosides

Syntheses of both 2′-amino-2′-ethynyl guanosine and uridine, using an intramolecular aminohydroxylation reaction as the key step, are described. The corresponding 5′-O-triphosphates of the aforementioned nucleosides were obtained and the inhibitory activity was subsequently evaluated against the hepatitis C virus NS5B polymerase.

Novel 2'-uridine azide and synthetic method thereof

The invention discloses novel 2'-uridine azide and a synthetic method thereof. The structural formula of the compound is as shown in specification, and reaction steps of the synthetic method of the novel 2'-uridine azide are as shown in specification. The

Antiviral nucleoside phosphoramidate and pharmaceutical composition and applications thereof

The invention provides an antiviral nucleoside phosphoramidate and a pharmaceutical composition and applications thereof. The nucleoside phosphoramidate compound is prepared by connecting nucleoside with phosphate through phosphorus-oxygen bonds. The structural formulas of the nucleoside phosphoramidate compound are represented by a, a1, a2, b, b1, and b2. The invention also discloses stereoisomers, pharmaceutically acceptable salts, hydrates, solvates, or crystals of the nucleoside phosphoramidate compound. The anti-hepatitis C activity of the provided novel nucleoside phosphoramidate is obviously better than that of sofosbuvir used in clinic. On the saccharide ring, the fluorine atoms are replaced by chlorine atoms, and the cytotoxicity of measure cell lines is prominently reduced. By systematically modifying and optimizing the basic groups, saccharide rings, and prodrugs, the anti-hepatitis C activity of partial synthesized compounds is 2 to 10 times higher than that of sofosbuvir. At the same time, the key parts of metabolism are optimized, the metabolism stability and chemical stability of synthesized compounds in plasma are better, compared with those of sofosbuvir.