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Trifluoromethylated Nucleosides : A Building Block Approach to Cytotoxic Adenosine Analogues

Trifluoromethylated Nucleosides : A Building Block Approach to Cytotoxic Adenosine Analogues

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DREXLER, Johannes, Ulrich GROTH, 2014. Trifluoromethylated Nucleosides : A Building Block Approach to Cytotoxic Adenosine Analogues. In: European Journal of Organic Chemistry. 2014(28), pp. 6314-6320. ISSN 0075-4617. eISSN 0365-5490

@article{Drexler2014Trifl-29311, title={Trifluoromethylated Nucleosides : A Building Block Approach to Cytotoxic Adenosine Analogues}, year={2014}, doi={10.1002/ejoc.201402755}, number={28}, volume={2014}, issn={0075-4617}, journal={European Journal of Organic Chemistry}, pages={6314--6320}, author={Drexler, Johannes and Groth, Ulrich} }

2014 Drexler, Johannes Trifluoromethylated Nucleosides : A Building Block Approach to Cytotoxic Adenosine Analogues 2014-11-26T09:43:23Z Groth, Ulrich Adenosine analogue nucleosides are a fundamental part of medicinal chemistry. Tubercidin is a well-known example, but its application is limited due to high toxicity. The development of less toxic synthetic analogues is therefore highly desirable. Here we show the synthesis of fluorinated nucleosides based on the pyrrolo[2,3-d]pyrimidine (7-deazapurine) motif. The synthetic approach is based on an easily accessible trifluoromethylated acetoacetate and several amidines, as building blocks. This allows for simultaneous introduction of a CF<sub>3</sub> group as well as a variety of C2 substituents for the synthesis of the heterocyclic part, including alkyl, aryl, SMe, Cl, N<sub>3</sub> and NH<sub>2</sub> moieties. Glycosylation of the fully pre-functionalized heterocycles proceeds with excellent β-selectivity. Cytotoxicities were determined using an AlamarBlue assay with HeLa S3 and Hep G2 cancer cell lines. The effect of C2 substitution was explored and a lead structure candidate with IC<sub>50</sub> values of 90 ± 49 nM (HeLa S3) and 28 ± 9 nM (Hep G2) was identified. Drexler, Johannes 2014-11-26T09:43:23Z eng Groth, Ulrich

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