1055030-23-3

Upstream product

• 79887-10-8 1-ethynyl-4-(n-pentyl)benzene 
• 1956-30-5 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 

Downstream Products

• 1055900-98-5 C₂₆H₂₉ClN₂O₇ 
• 1053616-55-9 acetic acid 2-acetoxymethyl-5-[2-oxo-6-(4-pentyl-phenyl)-2H-furo[2,3-d]pyrimidin-3-yl]-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Highly efficient AgNO3-catalyzed preparation of substituted furano-pyrimidine nucleosides

An efficient method for the synthesis of substituted furanopyrimidine nucleosides is described. Upon treatment with catalytic AgNO3, 5-alkynyl uracil derivatives were almost quantitatively converted into their corresponding bicyclic nucleoside

Extension of furopyrimidine nucleosides with 5-alkynyl substituent: Synthesis, high fluorescence, and antiviral effect in the absence of free ribose hydroxyl groups

A novel methodology to access alkynyl nucleoside analogues is elaborated. Highly fluorescent 5-alkynylfuropyrimidines were synthesized (97-46%) and their antiviral properties investigated in vitro. Regiochemistry of the functionalization was achieved with the aid of 5-endo-dig electrophilic halocyclization of acetyl 5-p-tolyl- or 5-p-pentylphenyl-2′-deoxyuridine. Structure of one of the resulting nucleosides, 6-p-tolyl-5-iodo-2′-deoxyribofuranosyl-furo[2,3-d]pyrimidin-2-one, was confirmed by X-ray crystallography, and its conformation was compared to related nucleosides. Diverse alkynyl substituents were introduced at the heterobicyclic base C-5 position via Sonogashira coupling of 5-iodo-2′-deoxyribofuranosyl-furo[2,3-d]pyrimidin-2-ones. The resulting compounds had fluorescence emissions of 452–481 nm. High quantum yields of 0.53–0.60 were observed for 9-ethynyl-9-fluorenol and propargyl alcohol/methyl ether-modified furopyrimidines. These modified nucleosides, designed in the form of ribose acetyl esters, are potential tools for fluorescent tagging, studying nucleoside metabolism, 2′-deoxyribonucleoside kinase activity, and antiviral activity. Antiviral assays against a broad spectrum of DNA and RNA viruses showed that in human embryonic lung (HEL) cell cultures some of the compounds showed antiviral activity (EC50 1.3–13.2 μM) against varicella-zoster virus (VZV). The alkynyl furopyrimidine with two p-pentylphenyl substituents emerged as the best compound with reasonable and selective anti-VZV activity, confirming p-pentylphenyl potency as a pharmacophore.