Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction

Koszytkowska‐Stawińska, Mariola; Sas, Wojciech

doi:10.1016/j.tet.2013.01.042

Cited by 15 publications

(12 citation statements)

References 29 publications

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“…Thus, the methods have already been applied to prepare some N-unsubstituted 1,2,3-triazoles. [32][33][34][35][36][37][38][39][40][41][42][43][44][45] Our previous studies were focused on the mechanisms to explain the formation of these heterocycles. [28][29][30][31] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Banert¹,

Hagedorn²,

Hemeltjen³

et al. 2016

Arkivoc

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About thirty NH-1,2,3-triazoles with at least one additional functional group in a side chain at C-4 were prepared from propargyl substrates. These reactions included propargyl azides and their [3,3]-sigmatropic rearrangement to generate short-lived allenyl azides, which cyclized to form triazafulvenes that could be trapped by addition of N-or O-nucleophiles. In most cases, simple substrates and cheap sodium azide were utilized as starting compounds, and the syntheses were performed by using a one-pot procedure without isolation of any dangerous azides. This method to prepare NH-1,2,3-triazoles turned out to be compatible with quite different substitution patterns of the propargyl substrate.

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Section: Introductionmentioning

confidence: 99%

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Banert¹,

Hagedorn²,

Hemeltjen³

et al. 2016

Arkivoc

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“…The applicability of a 1,2,3-triazole ring as a replacement of sugar [17][18][19] or nucleobase moieties 17,[19][20][21] as well as an additional linker between a phosphonoalkyl unit and a nucleobase has been widely explored [22][23][24][25][26][27][28] including our achievements. The applicability of a 1,2,3-triazole ring as a replacement of sugar [17][18][19] or nucleobase moieties 17,[19][20][21] as well as an additional linker between a phosphonoalkyl unit and a nucleobase has been widely explored [22][23][24][25][26][27][28] including our achievements.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues

Głowacka

Balzarini

Andrei

et al. 2014

Bioorganic & Medicinal Chemistry

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The efficient synthesis of a new series of polyhydroxylated dibenzyl ω-(1H-1,2,3-triazol-1-yl)alkylphosphonates as acyclic nucleotide analogues is described starting from dibenzyl ω-azido(polyhydroxy)alkylphosphonates and selected alkynes under microwave irradiation. Selected O,O-dibenzylphosphonate acyclonucleotides were transformed into the respective phosphonic acids. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses and for cytostatic activity against murine leukemia L1210, human T-lymphocyte CEM and human cervix carcinoma HeLa cells. Compound (1S,2S)-16b exhibited antiviral activity against Influenza A H3N2 subtype (EC50=20μM-visual CPE score; EC50=18μM-MTS method; MCC >100μM, CC50 >100μM) in Madin Darby canine kidney cell cultures (MDCK), and (1S,2S)-16k was active against vesicular stomatitis virus and respiratory syncytial virus in HeLa cells (EC50=9 and 12μM, respectively). Moreover, compound (1R,2S)-16l showed activity against both herpes simplex viruses (HSV-1, HSV-2) in HEL cell cultures (EC50=2.9 and 4μM, respectively) and feline herpes virus in CRFK cells (EC50=4μM) but at the same time it exhibited cytotoxicity toward uninfected cell (MCC⩾4μM). Several other compounds have been found to inhibit proliferation of L1210, CEM as well as HeLa cells with IC50 in the 4-50μM range. Among them compounds (1S,2S)- and (1R,2S)-16l were the most active (IC50 in the 4-7μM range).

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“…Koszytkowska-Stawinska et al. also synthesized triazole fleximers utilizing the Bannert cascade reaction, 65 which involves a [3,3]-sigmatropic rearrangement ( Scheme 3 ); however, these analogues contained a methylene group between the azide and the pyrimidine moieties ( Scheme 3 ). They synthesized several ribose analogues, as well as some acyclic phosphonate analogues; however, no biological activity was included in their report.…”

Section: Initial Resultsmentioning

confidence: 99%

“…They synthesized several ribose analogues, as well as some acyclic phosphonate analogues; however, no biological activity was included in their report. 65 …”

Section: Initial Resultsmentioning

confidence: 99%

Flexibility—Not just for yoga anymore!

Seley‐Radtke

2018

Antivir Chem Chemother

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Over the past few years, nucleosides have maintained a prominent role as one of the cornerstones of antiviral and anticancer therapeutics, and many approaches to nucleoside drug design have been pursued. One such approach involves flexibility in the sugar moiety of nucleosides, for example, in the highly successful anti-HIV and HBV drug tenofovir. In contrast, introduction of flexibility to the nucleobase scaffold has only more recently gained significance with the invention of our fleximers. The history, development, and some biological relevance for this innovative class of nucleosides are detailed herein.

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Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction

Cited by 15 publications

References 29 publications

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues

Flexibility—Not just for yoga anymore!

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