428509-97-1Relevant academic research and scientific papers
Synthesis of dicobalt hexacarbonyl 5-p-tolylethynyl-2′-deoxyuridine
Esho, Noor,Davies, Brian,Lee, Janet,Dembinski, Roman
, p. 332 - 333 (2002)
Reactions of 5-p-tolylethynyl-2′-deoxyuridine and 3′,5′-diO-acetyl-5-p-tolylethynyl-2′-deoxyuridine with Co2(CO)8 in THF gave 5-p-tolC2[Co2(CO)6]-2′-deoxyuridine and 3′,5′-diO-acetyl-5-p-tolC2[Co2(CO) 6]-2′-deoxyuridine (92 and 66%).
Extension of furopyrimidine nucleosides with 5-alkynyl substituent: Synthesis, high fluorescence, and antiviral effect in the absence of free ribose hydroxyl groups
Kaczmarek, Renata,Twardy, Dylan J.,Olson, Trevor L.,Korczyński, Dariusz,Andrei, Graciela,Snoeck, Robert,Dolot, Rafa?,Wheeler, Kraig A.,Dembinski, Roman
supporting information, (2020/10/13)
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.
Zinc-catalyzed cycloisomerizations. Synthesis of substituted furans and furopyrimidine nucleosides
Sniady, Adam,Durham, Audrey,Morreale, Marco S.,Marcinek, Andrzej,Szafert, Slawomir,Lis, Tadeusz,Brzezinska, Krystyna R.,Iwasaki, Takanori,Ohshima, Takashi,Mashima, Kazushi,Dembinski, Roman
, p. 5881 - 5889 (2008/12/21)
(Chemical Equation Presented) 5-Endo-dig cycloisomerization of 1,4- and 1,2,4- mostly aryl-substituted but-3-yn-1-ones in the presence of a catalytic amount of zinc chloride etherate (10 mol %) in dichloromethane at room temperature gave 2,5-di- and 2,3,5
