ArticleTetrahedron2017
Efficient diastereoselective synthesis of a new class of azanucleosides: 2'-homoazanucleosides.
Article in Tetrahedron, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- From Chemoenzymatic Synthesis to Biological Effects: Enantiomerically Enriched Vanillin-Derived δ-Iodo-γ-Lactones as Modulators of Cancer Cell Viability and Inducers of Cell Death.International journal of molecular sciences · 2026Article
- Synthetic Modifications of a PbMolecules (Basel, Switzerland) · 2024Article
- Membrane-Active Thermoresponsive Block Copolymers Containing a Diacylglycerol-Based Segment: RAFT Synthesis, Doxorubicin Encapsulation, and Evaluation of Cytotoxicity against Breast Cancer Cells.Biomacromolecules · 2023Article
- Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues.Molecules (Basel, Switzerland) · 2020Review
- Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors inBeilstein journal of organic chemistry · 2018Article
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3 authors.
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Abstract
Azanucleosides, sugar-modified nucleoside analogues containing a 4' nitrogen atom, have shown a lot of therapeutic potential, e.g. as anti-cancer and antiviral agents. We report the synthesis of a series of 2'-homoazanucleosides, in which the nucleobase is attached to the 2'-position of the pyrrolidine ring via a methylene linker. A suitable orthogonally protected iminosugar was synthesized by ring closing metathesis and dihydroxylation as key steps and further converted to a series of 8 nucleoside analogues through Mitsunobu reaction with suitably protected nucleobases. The 5' position of the adenine analogue was then further derivatized with thiols to afford 2 additional compounds. The final compounds were evaluated for biological activity.
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