<i>N(3)</i>‐Protection of Thymidine with Boc for an Easy Synthetic Access to Sugar‐Alkylated Nucleoside Analogs

Simeone, Luca; Napoli, Lorenzo De; Montesarchio, Daniela

doi:10.1002/cbdv.201100103

Cited by 9 publications

(6 citation statements)

References 29 publications

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“…Nucleoside 2, known in the literature since the late 70s, 19 has been recently prepared by some of us following a new, optimized protocol, requiring only straightforward and high yielding steps, 20 based on the use of Boc as a transient protecting group on the N-3 position. 21 Following our synthetic scheme, modified nucleoside 2 was obtained in 6 steps with 50% overall yield starting from uridine.…”

Section: Resultsmentioning

confidence: 99%

A new design for nucleolipid-based Ru(iii) complexes as anticancer agents

et al. 2013

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In continuation with our studies concerning the synthesis, characterization and biological evaluation of nucleolipidic Ru(III) complexes, a novel design for this family of potential anticancer agents is presented here. As a model compound, a new uridine-based nucleolipid has been prepared, named HoUrRu, following a simple and versatile synthetic procedure, and converted into a Ru(III) salt. Stable formulations of this highly functionalized Ru(III) complex have been obtained by co-aggregation with either the zwitterionic lipid POPC or the cationic DOTAP, which have been subjected to an in-depth microstructural characterization, including DLS, SANS and EPR measurements. The in vitro bioactivity profile of HoUrRu, as a pure compound or in formulation with POPC or DOTAP, reveals high antiproliferative activity against MCF-7 and WiDr human cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

A new design for nucleolipid-based Ru(iii) complexes as anticancer agents

et al. 2013

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“…In most cases they have become important drugs [1,2,3,4,5,6]. In summary they are molecules that stimulate intense research aimed at the development of new structural analogues possessing potential regulatory or pharmacological activities [7,8,9,10,11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Acadesine (AICA-riboside) Analogues Having Acyclic d-Ribityl or 4-Hydroxybutyl Chains in Place of the Ribose

et al. 2013

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Abstract:The antiviral activity of certain acyclic nucleosides drew our attention to the fact that the replacement of the furanose ring by an alkyl group bearing hydroxyl(s) could be a useful structural modification to modulate the biological properties of those nucleosides. Herein, we report on the synthesis of some novel acadesine analogues, where the ribose moiety is mimicked by a D-ribityl or by a hydroxybutyl chain.

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“…[29] To do so, we converted nucleoside 2 a (Scheme 3) to the corresponding N3-Boc-protected analog 7 under standard conditions (Scheme 5). Removal of the O-acetyl protecting group under basic conditions [32] followed by treatment with methyl propynoate in the presence of catalytic amounts of DMAP yielded nucleoside 9 as an inseparable mixture of stereoisomers. [29] Deprotection of the DMTr and Boc protecting groups produced 10 in good yields.…”

Section: Design and Synthesis Of Blocked Nucleosides And Nucleotidesmentioning

confidence: 99%

2’,3’‐Protected Nucleotides as Building Blocks for Enzymatic de novo RNA Synthesis

Pichon,

Levi‐Acobas,

Kitoun

et al. 2024

Chemistry A European J

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Besides being a key player in numerous, fundamental biological process, RNA also represents a versatile platform for the creation of therapeutic agents and efficient vaccines. The production of RNA oligonucleotides, especially those decorated with chemical modifications, cannot meet the exponential demand. Due to the inherent limits of solid‐phase synthesis and in vitro transcription, alternative, biocatalytic approaches are in dire need to facilitate the production of RNA oligonucleotides. Here, we present a first step towards the controlled enzymatic synthesis of RNA oligonucleotides. We have explored the possibility of a simple protection step of the vicinal cis‐diol moiety to temporarily block ribonucleotides. We demonstrate that pyrimidine nucleotides protected with acetals, particularly 2',3'‐O‐isopropylidene, are well‐tolerated by the template‐independent RNA polymerase PUP (polyU polymerase) and highly efficient coupling reactions can be achieved within minutes – an important feature for the development of enzymatic de novo synthesis protocols. Even though purines are not equally well‐tolerated, these findings clearly demonstrate the possibility of using cis‐diol‐protected ribonucleotides combined with template‐independent polymerases for the stepwise construction of RNA oligonucleotides.

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N(3)‐Protection of Thymidine with Boc for an Easy Synthetic Access to Sugar‐Alkylated Nucleoside Analogs

Cited by 9 publications

References 29 publications

A new design for nucleolipid-based Ru(iii) complexes as anticancer agents

A new design for nucleolipid-based Ru(iii) complexes as anticancer agents

Synthesis of New Acadesine (AICA-riboside) Analogues Having Acyclic d-Ribityl or 4-Hydroxybutyl Chains in Place of the Ribose

2’,3’‐Protected Nucleotides as Building Blocks for Enzymatic de novo RNA Synthesis

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