3263-91-0

Basic information

• Product Name: Uridine, 5-bromo-, 2',3',5'-tribenzoate
• CAS NO: 3263-91-0
• Molecular Formula: C30H23BrN2O9
• Molecular Weight: 635.425
• Mol File: 3263-91-0.mol

Chemical Properties

• CAS DataBase Reference: Uridine, 5-bromo-, 2',3',5'-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 5-bromo-, 2',3',5'-tribenzoate(3263-91-0)
• EPA Substance Registry System: Uridine, 5-bromo-, 2',3',5'-tribenzoate(3263-91-0)

Safety Data

• Hazardous Substances Data: 3263-91-0(Hazardous Substances Data)

Usage

Uses

Used in Research and Biochemical Studies:
Uridine, 5-bromo-, 2',3',5'-tribenzoate is used as a precursor for the synthesis of various nucleoside analogs, which are essential for the development of new drugs and therapeutic agents. Its unique structure allows for the modification and functionalization of nucleosides, enabling the exploration of their potential applications in medicine and biotechnology.
Used in Pharmaceutical Development:
As a potential therapeutic agent, Uridine, 5-bromo-, 2',3',5'-tribenzoate is being investigated for its potential use in the treatment of neurological disorders. Its ability to modulate cellular processes and interact with specific biological targets makes it a promising candidate for the development of novel treatments for various neurological conditions.
Used in Nucleic Acid and RNA Research:
Uridine, 5-bromo-, 2',3',5'-tribenzoate serves as a useful tool for investigating the structure and function of nucleic acids and RNA. Its unique benzoylated form allows researchers to study the interactions between nucleosides and other biomolecules, providing valuable insights into the mechanisms of gene expression, regulation, and disease pathogenesis.

Upstream product

• 613-90-1 benzoyl cyanide 
• 957-75-5 5-bromouridine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 33282-64-3 2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine 

Relevant articles and documents

Inhibition of tyrosyl-DNA phosphodiesterase 1 by lipophilic pyrimidine nucleosides

Inhibition of DNA repair enzymes tyrosyl-DNA phosphodiesterase 1 and poly(ADP-ribose) polymerases 1 and 2 in the presence of pyrimidine nucleoside derivatives was studied here. New effective Tdp1 inhibitors were found in a series of nucleoside derivatives possessing 2′,3′,5′-tri-O-benzoyl-d-ribofuranose and 5-substituted uracil moieties and have half-maximal inhibitory concentrations (IC50) in the lower micromolar and submicromolar range. 2′,3′,5′-Tri-Obenzoyl- 5-iodouridinemanifested the strongest inhibitory effect on Tdp1 (IC50 = 0.6 μM). Adecrease in the number of benzoic acid residues led to a marked decline in the inhibitory activity, and pyrimidine nucleosides lacking lipophilic groups (uridine, 5-fluorouridine, 5-chlorouridine, 5-bromouridine, 5-iodouridine, and ribothymidine) did not cause noticeable inhibition of Tdp1 (IC50 > 50 μM). No PARP1/2 inhibitors were found among the studied compounds (residual activity in the presence of 1mMsubstances was 50-100%). Several O-benzoylated uridine and cytidine derivatives strengthened the action of topotecan on HeLa cervical cancer cells.

A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation

A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.

NEW PRODUCTION METHOD FOR PYRIMIDINE NUCLEOSIDE DERIVATIVES

PROBLEM TO BE SOLVED: To provide a method for producing pyrimidine nucleoside derivatives with excellent handleability. SOLUTION: A glycosyl donor of which OH groups at positions 1 and 2 are acylated and other OH groups are protected and a silylated pyrimidine derivative are reacted in the presence of an acid azole/pyridine conjugate of the following general formula (1) or (2) and a solvent. Acid azole/pyridine conjugate is excellent in handleability because it has no or low hygroscopicity. In the formula (1), A is -O- or -S-, in the formulae (1) and (2), R1-R8 are hydrocarbon groups which may be substituted, R1-R8 may form a ring by binding to other R1-R8, the acid azole/pyridine conjugate may comprise plurality of formula (1) and/or formula (2) as partial structures. Further, it may be bonded to a carrier via R1-R8. COPYRIGHT: (C)2015,JPO&INPIT

Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate

Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5- phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales.