77887-20-8

Usage

Uses

Used in Biochemical Research:
Uridine, 2'-deoxy-5-(phenylethynyl)is used as a molecular probe for studying the structure and function of RNA due to its unique chemical modifications that allow for specific interactions and analyses within RNA molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, this modified nucleoside is utilized in the development of novel oligonucleotide-based therapeutics, potentially leading to new treatments for various diseases and conditions.
Used in Neuroscience and Neuropharmacology:
Uridine, 2'-deoxy-5-(phenylethynyl)is used as a subject of research for its potential neuroprotective and cognitive-enhancing effects, which could contribute to advancements in the understanding and treatment of neurological disorders and cognitive impairments.
Used in Therapeutic Applications:
The phenylethynyl modification of uridine may alter its interactions with biological processes, making it a candidate for exploration in therapeutic applications, particularly in conditions where neuroprotection and cognitive enhancement are desired outcomes.

Upstream product

• 78824-34-7 5-Phenylethynyl-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 536-74-3 phenylacetylene 
• 151361-85-2 5-(Trifluoromethanesulfonyloxy)-2'-deoxyuridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 1956-30-5 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine 
• 31356-86-2 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil 
• 5168-36-5 5-hydroxy-2'-deoxyuridine 
• 943446-57-9 C₂₁H₂₀N₂O₇ 
• 77875-92-4 C₃₃H₂₈N₂O₇ 
• 78824-31-4 di-O-trimethylsilyl-5-iodo-2'-deoxyuridine 

Downstream Products

• 319425-61-1 3-(2′-deoxy-β-D-ribofuranosyl)-6-(phenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one 
• 946148-16-9 5-phenylethynyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 

Relevant academic research and scientific papers

Efficient sonogashira coupling of unprotected halonucleosides in aqueous solvents using water-soluble palladium catalysts

A variety of applications of C-alkynylated nucleosides has prompted the continuing development of efficient synthetic methods for their preparation. We report an efficient and environmentally benign Sonogashira coupling reaction for alkynylation of unprotected halonucleosides in an aqueoussolvent. The combination of Pd(OAc)2, CuI, and TXPTS [trisodium tri(2,4-dimethyl-5-sulfonatophenyl)phosphane] provided an effective catalyst for the alkynylation of 8-bromo-purines and 5-iodouridine in H2O/CH 3CN (1:1) in yields ranging from 42 to 98%.

Oligodeoxynucleotides incorporating structurally simple 5-alkynyl-2′-deoxyuridines fluorometrically respond to hybridization

Selected 5-ethynyl derivatives of 2′-deoxyuridine are shown to fluorometrically respond to hybridization and selectively base-pair to adenine whilst maintaining duplex stability. The Royal Society of Chemistry.

Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria

We herein report a new category of 5-substituted pyrimidine nucleosides as potent inhibitors of mycobacteria. A series of 5-alkynyl derivatives of 2′-deoxyuridine (1-8), 2′-deoxycytidine (9-14), uridine (15-17), and 2′-O-methyluridine (18, 19) were synthe

Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain

In addition to our recent report on the potent anti-varicella-zoster virus (VZV) activity of some unusual bicyclic furopyrimidine nucleosides bearing long alkyl side chains, we herein report the further significant enhancement of the antiviral potency by

Nucleic Acid Related Compounds. 39. Efficient Conversion of 5-Iodo to 5-Alkynyl and Derived 5-Substituted Uracil Bases and Nuleosides

Coupling of terminal alkynes with 5-iodo-1-methyl-uracil and 5-iodouracil nucleosides (protected as their p-toluyl esters) proceeded in high yields in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I)iodide in warm triethylamine.Several of the subsequently deprotected 5-alkynyl-2'-deoxyuridines, including the parent 5-ethynyl-2'-deoxyuridine, had antiviral activity, and their 5'-monophosphates inhibited thymidylate synthetase.Hydrogenation of the 5-alkynyl side chain can be controlled to give (Z)-5-alkenyl- or the saturated 5-alkyl-2'-deoxyuridines.This provides a stereocontrolled route to the known 5-ethyl-and 5-n-hexyl-2'-deoxyuridines as well as (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU).Hydration of the triple bond gave the corresponding uracil-5-alkanone products in favorable cases.

NUCLEIC ACID RELATED COMPOUNDS. 31. SMOOTH AND EFFICIENT PALLADIUM-COPPER CATALYZED COUPLING OF TERMINAL ALKYNES WITH 5-IODOURACIL NUCLEOSIDES

Coupling of terminal alkynes with protected 5-iodouracil nucleosides in the presence of dichlorobis(triphenylphosphine)palladium and copper(I) iodide in triethylamine gives the corresponding 5-(alkyn-1-yl)uracil nucleosides in 72-92percent yields.

ALCYNYL-5 DESOXY-2' URIDINES PAR COUPLAGES D'ORGANOZINCIQUES ACETYLENIQUES AVEC L'IODO-5 O-3',5'-BIS(TRIMETYLSYLYL) DESOXYURIDINE, CATALYSES PAR DES COMPLEXES ORGANOPALLADIES ET DE NICKEL

5-Alkynyl 2'-deoxyuridines are obtained in low to modest yields by the palladium and Nickel catalyzed reaction of alkynylzinc reagents with O-3',5'-bis(trimethylsilyl) deoxyuridine in T.H.F.