25692-02-8

Usage

Derived from uridine

2',3',5'-Tri-O-benzoyl-5-ethyluridine is a chemical compound that is derived from uridine, a nucleoside found in RNA.

Three benzoyl groups

It is characterized by three benzoyl groups attached to the 2', 3', and 5' positions of the ribose sugar.

Ethyl group attached

It also has an ethyl group attached to the 5' position.

Potential applications in organic synthesis and medicinal chemistry

Due to its unique structure and reactivity, 2',3',5'-Tri-O-benzoyl-5-ethyluridine has potential applications in organic synthesis and medicinal chemistry.

Building block for modified nucleosides and nucleotides

It can be used as a building block for the preparation of modified nucleosides and nucleotides.

Nucleoside-based antiviral and anticancer drugs

It can also be used in the development of nucleoside-based antiviral and anticancer drugs.

Selective removal of benzoyl groups

Its benzoyl groups can be selectively removed to reveal the free hydroxyl groups, providing further versatility in its use as a chemical reagent.

Upstream product

• 56367-98-7 5-ethyl-cytidine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 31167-05-2 2,4-bis-trimethylsilyloxy-5-ethylpyrimidine 
• 4212-49-1 5-ethyluracil 
• 22224-38-0 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 

Downstream Products

• 214482-11-8 5-ethyl-2',3',5'-tris-O-benzoyl-4-thiouridine 
• 1613530-28-1 C₃₂H₂₉N₃O₈ 
• 1613530-27-0 C₃₄H₂₉N₅O₈ 

Relevant academic research and scientific papers

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

5-Substituted UTP derivatives as P2Y2 receptor agonists

A series of 5-alkyl-substituted UTP derivatives, which had been synthesized previously with a moderate degree of purity, was resynthesized, purified, and characterized. Synthetic and purification procedures were optimized. New spectroscopic data, including 13C- and 31P NMR data, are presented. Phosphorylation reactions yielded a number of side products, such as the 2'-, 3'-, and 5'-monophosphates, the 2',3'-cyclic monophosphates, and the 2',3'-cyclic phosphates of the 5'-triphosphates. Furthermore, raw products were contaminated with inorganic phosphates, including cyclometatriphosphate, phosphate, and pyrophosphate. The uracil nucleotides were investigated for their potency to increase intracellular calcium concentrations by stimulation of P2Y2 receptors (P2Y2R) on NG108- 15 cells, a mouse neuroblastoma x glioma cell line, and in human basal epithelial airway cells, including a cystic fibrosis (CF/T43) cell line. UTP exhibited EC50 values of ca. 1 μM (in NG108-15 cells) and of 0.1 μM (in CF/T43 cells), respectively. 5-Substituted UTP derivatives were agonists at the P2Y2R, but were less potent than UTP. 5-Ethyl-UTP, for example, exhibited an EC50 value of 99 μM at P2Y2R of NG108-15 cells and proved to be a full agonist. With increasing volume of the 5- substituent of UTP derivatives, P2Y2 activity decreased.

Process for the preparation of 5-(2-bromovinyl)-uridine

The invention relates to (E)-5-(2-bromovinyl)-uridine and its derivatives of general formula VI, STR1 wherein R1 stands for a hydrogen atom, C1-8 alkanoyl group, benzoyl group or a benzoyl group substituted in para position either with a C1-4 alkyl group or a halogen atom, and a process for preparing them by brominating 2',3',5'-tri-O-acyl-5-ethyl-uridine of general formula IV, STR2 wherein R is identical with R1, except where R1 stands for a hydrogen atom, dehydrohalogenating the resulting dibromo compound of general formula V STR3 and optionally deacylating it. The resulting compounds of general formula VI are exhibiting significant potency against Herpes simplex virus species and are of remarkably low acute toxicity.