Efficient Synthesis of Novel 4'-Trifluoromethyl-5'-norcarbocyclic Purine Phosphonic Acid Analogs by Using the Ruppert-Prakash Reaction

Kim, Seyeon; Kim, Eunae; Yoo, Jin Cheol; Hong, Joon Hee

doi:10.5012/bkcs.2014.35.9.2743

Cited by 3 publications

(1 citation statement)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hong's group reported a series of racemic 5'norcarbanucleosides [74][75][76] including a phosphonate analog of 2'-modified 5'-norcarbocyclic adenine. [77] But-3-en-1-ol 201 was transformed into three steps to (�)À 202, (Scheme 31).…”

Section: '-Norcarbanucleosidesmentioning

confidence: 99%

Chemical Approaches to Carbocyclic Nucleosides

Ojeda‐Porras

Roy

Agrofoglio

2022

The Chemical Record

View full text Add to dashboard Cite

Nucleoside analogues are at the forefront of antiviral therapy for last decades. To circumvent some of their limitations, based on their metabolism, and in order to improve their anti‐viral potency and selectivity, several families of nucleoside analogues have been described through structural modifications at the sugar and heterocycles. The replacement of the oxygen of the nucleoside by a methylene has led to the family of carbocyclic (or cyclopentane) nucleoside analogues. Various potent anti‐HIV and anti‐HBV drugs belong to this family. Main syntheses of carbocyclic analogues of nucleosides used Diels‐Alder reactions (in racemic or asymmetric series), but also started from carbohydrates (ribose, glucose), as a source of optically active compounds, which then had to be transformed into carbacycles under various conditions. The growing interest in carbocyclic nucleosides has led several groups, including ours, to develop new analogues and to explore novel routes. This article will review some of the recent chemistry developed on selected five‐membered ring carbocyclic nucleosides.

show abstract

Section: '-Norcarbanucleosidesmentioning

confidence: 99%

Chemical Approaches to Carbocyclic Nucleosides

Ojeda‐Porras

Roy

Agrofoglio

2022

The Chemical Record

View full text Add to dashboard Cite

show abstract

Recent advances in the synthesis of cyclic 5′-nornucleoside phosphonate analogues

Shen

Hong

2018

Carbohydrate Research

View full text Add to dashboard Cite

Synthesis of Novel 4′-Trifluoromethyl-5′-NorcarbocyclicC-Nucleoside Phosphonic Acids as Potent Anti-Leukemic Agents

Kim

Hong

2015

Nucleosides, Nucleotides and Nucleic Acids

View full text Add to dashboard Cite

The syntheses of novel C-nucleoside phosphonic acids as potential antiviral agents are described. The sugar moiety that served as the nucleoside skeleton was produced starting from commercially available 1,3-dihydroxy cyclopentane. The key C-C bond formation from sugar to base precursor was performed using the Knoevenagel-type condensation. The synthesized compounds exhibited anti-HIV activity and cytotoxicity. Also, the synthesized compounds were screened in vitro for tumor growth inhibitory activity against mouse leukemia cell lines (L-1210, P-815).

show abstract

Efficient Synthesis of Novel 4'-Trifluoromethyl-5'-norcarbocyclic Purine Phosphonic Acid Analogs by Using the Ruppert-Prakash Reaction

Cited by 3 publications

References 42 publications

Chemical Approaches to Carbocyclic Nucleosides

Chemical Approaches to Carbocyclic Nucleosides

Recent advances in the synthesis of cyclic 5′-nornucleoside phosphonate analogues

Synthesis of Novel 4′-Trifluoromethyl-5′-NorcarbocyclicC-Nucleoside Phosphonic Acids as Potent Anti-Leukemic Agents

Contact Info

Product

Resources

About