Flexible Nucleobase Analogues: Novel Tools for Exploring Nucleic Acids

Zimmermann, Sarah C.; Seley‐Radtke, Katherine L.

doi:10.1007/978-3-642-54452-1_9

Cited by 2 publications

(1 citation statement)

References 69 publications

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“…24 The correlation between the biological properties and structural features of "flexible" nucleobases was discussed in a monograph published in 2014. 28 Acyclic bitriazole nucleosides 24 (Scheme 10) exhibited antiproliferative activity against the drug-resistant pancreatic cancer cell line MIA PaCa-2, which is associated with caspase-dependent apoptosis. These compounds were also characterized with respect to their immunomodulatory properties.…”

Section: The Biological Activity Of Fleximersmentioning

confidence: 99%

Nucleoside Analogs with Fleximer Nucleobase

Chudinov

2020

Chem Heterocycl Comp

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This review article is devoted to the so-called fleximer nucleoside analogs, containing two or more planar moieties in the heterocyclic base, connected by a bond that permits rotation. Such analogs have been proposed as molecular probes for detecting enzyme-substrate interactions and studying the transcription and translation of nucleic acids, but subsequently have attracted the interest of researchers by their antiviral and antitumor activity. The methods used in the synthesis of such compounds, along with their structural features and also biological activity are considered in this review.

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Section: The Biological Activity Of Fleximersmentioning

confidence: 99%

Nucleoside Analogs with Fleximer Nucleobase

Chudinov

2020

Chem Heterocycl Comp

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New Metal‐Free Route towards Imidazole‐Substituted Uridine

et al. 2020

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Nucleosides with a bi(hetero)aryl nucleobase have unique potential applications as antiviral drugs and molecular probes. The need for transition metal catalysis to synthesize these nucleosides from pre‐functionalized building blocks and the use of nucleobase protection groups results in expensive and tedious syntheses. Herein we report that 5‐imidazolyl‐uracil can be obtained by scalable Van Leusen imidazole synthesis and regioselectively introduced on ribose to obtain the desired nucleoside in a 5 step synthesis (total yield 55 %). The 5‐imidazolyl moiety leads to improved fluorescence properties. The only side‐product formed was characterized by 2D‐NMR and X‐ray crystallography and could be suppressed during synthesis in favor of the desired product.

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Flexible Nucleobase Analogues: Novel Tools for Exploring Nucleic Acids

Cited by 2 publications

References 69 publications

Nucleoside Analogs with Fleximer Nucleobase

Nucleoside Analogs with Fleximer Nucleobase

New Metal‐Free Route towards Imidazole‐Substituted Uridine

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