Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)

Yu, Jinha; Kim, Gyudong; Jarhad, Dnyandev B.; Kim, Hong Rae; Jeong, Lak Shin

doi:10.1007/s12272-019-01157-6

Cited by 3 publications

(5 citation statements)

References 17 publications

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“…Since selenosugars frequently exhibit greater biological activities than the corresponding sulfur analogues, ,− the 4-selenothreose derivatives synthesized in this study will be attractive as new-type building blocks for selenosugar-based drugs with versatile bioactivities. Their incorporation into threose nucleic acid, which is an artificial nucleic acid capable of carrying the genetic information, , will also be an intriguing challenge for developing novel variants of TNA.…”

Section: Discussionmentioning

confidence: 99%

“…In the meantime, Pinto and co-workers , succeeded in the stereoselective synthesis of a series of 4′-seleno- d -ribonucleosides ( 4 ) and applied the thymidine variant to the synthesis of oligonucleotides, which revealed a unique conformational shift arising from the introduced selenonucleoside. Thus, selenosugars and selenonucleosides are interesting targets of organic synthesis as they would possess potential biological activities, such as enzyme inhibitors, , antioxidants, , antibiotics, − and so forth . However, 4-selenotherofuranose derivatives, which have trans configuration for the two dihydroxy substituents at the 2,3-positions such as 2 and 3a and a glycoside bond at the anomeric position, are not available in the current selenosugar library.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate

et al. 2021

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Selenosugars are interesting targets of organic synthesis as they would possess potential biological activities. However, 4-selenotherofuranose derivatives, which have trans configuration for the two dihydroxy substituents at the 2,3-positions and a glycoside bond at the anomeric position, are not available in the current selenosugar library. In this study, racemic 4-selenothreofuranose derivatives were synthesized from trans-3,4-dioxygenated tetrahydroselenophenes in 77–99% yields with the α/β selectivity about 7:3 via oxidation and subsequent seleno-Pummerer rearrangement. The acetoxy group introduced at the anomeric position was then substituted with various nucleophiles, including activated 6-chloropurine, which afforded 4′-selenothreonucleoside derivatives, in the presence of BF3·OEt2 or TMSOTf. The stereochemistry of the selenosugar products was established by 1H NMR spectroscopy as well as X-ray analysis. The similar α/β selectivity observed in the latter glycosylation reaction to that in the former seleno-Pummerer rearrangement suggested the mediation of a common selenonium intermediate (−Se+C<). It was also suggested that an unexpected interaction between the ester protecting group at the 3-position of the selenofuranose ring and the anomeric carbon atom decreases the α/β selectivity.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate

et al. 2021

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“…It might work well as a biological contrast agent, because it is a multiphoton‐stimulated PDT reagent. Even though selenium‐containing chiral drugs have shown promise in fighting cancer, Jeong was not able to make L‐2′,3′‐dideoxy‐4′‐selenonucleosides that is effective against HIV [70] . All of the synthesized products did not show any anticancer action.…”

Section: Application Of Chiral Organic Selenidesmentioning

confidence: 97%

“…Even though selenium-containing chiral drugs have shown promise in fighting cancer, Jeong was not able to make L-2',3'-dideoxy-4'-selenonucleosides that is effective against HIV. [70] All of the synthesized products did not show any anticancer action. This shows that the way chiral drugs are shaped can make a big difference in how well they work.…”

Section: In Biomedical Fieldmentioning

confidence: 99%

Recent Progress in Synthesis and Application of Chiral Organoselenium Compounds

Lai,

Liang,

Zeng

2024

Chemistry A European J

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Chiral organoselenium compounds have shown an important role as intermediates in many areas, such as drug discovery, organic catalysis, and nanomaterials. A lot of different methods have been developed to synthesize chiral compounds which contain selenium, because they have interesting properties and can be used in real life. Over the last few decades, a lot of progress has been made in making chiral organoselenium compounds synthetically. This work gives an overview of the progress made in creating new ways to synthesize chiral organoselenium compounds by categorizing them into groups based on the reactions they undergo. In addition, the use of chiral organoselenium compounds is also discussed.

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“…Subsequent work extended the scope of this process to purine nucleosides [106b] . The products were assayed for potential anti‐HIV activity, but proved poorly effective [106c] . Wojaczyńska et al [107] .…”

Section: Asymmetric Reactions Of Selenium Nucleophilesmentioning

confidence: 99%

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Stadel,

Back

2024

Chemistry A European J

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The discovery and synthetic applications of novel organoselenium compounds and their reactions proceeded rapidly during the past fifty years and such processes are now carried out routinely in many laboratories. At the same time, the growing demand for new enantioselective processes provided new challenges. The convergence of selenium chemistry and asymmetric synthesis led to key developments in the 1970s, although the majority of early work was based on stoichiometric processes. More recently, greater emphasis has been placed on greener catalytic variations, along with the discovery of novel reactions and a deeper understanding of their mechanisms. The present review covers the literature in this field from 2010 to early 2023 and encompasses asymmetric reactions mediated by chiral selenium‐based reagents, auxiliaries and, especially, catalysts. Protocols based on achiral selenium compounds in conjunction with other species of chiral catalysts, as well as reactions that are controlled by chiral substrates, are also included.

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Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)

Cited by 3 publications

References 17 publications

Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate

Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate

Recent Progress in Synthesis and Application of Chiral Organoselenium Compounds

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

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