Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties

Pejanović, Vjera; Stokic, Zdenka; Stojanović, Biljana; Piperski, Vesna; Popsavin, Mirjana; Popsavin, Velimir

doi:10.1016/s0960-894x(03)00289-0

Cited by 13 publications

(4 citation statements)

References 19 publications

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“…The corresponding L -4′-thionucleosides ( Figure 5 , 9a – d ) were synthesized by starting from 1,2,3,5-tetra-O-acetyl-4-thio-β-L-ribofuranose [ 52 ]. All tested compounds showed a moderate growth inhibitory activity against HTB14 human glioma cells.…”

Section: Nucleoside Analogs As Therapeutic Antiviral and Antitumor Agentsmentioning

confidence: 99%

“…Above, we listed some of the L -nucleoside analogues with a solid demonstration of their therapeutic activities, which are summarized in Table 1 . Besides, there are many other nucleoside-like small molecules designed and evaluated as antiviral therapeutics, which had an L -configuration similar to its modified nucleoside, including cyclobutene L -nucleoside analogues [ 72 ], L -erythro-hexopyranosyl nucleosides [ 73 , 74 ], L -4′-C-ethynyl-2′-deoxypurine nucleosides [ 75 ], L -ribo-configured Locked Nucleic Acid [ 76 , 77 , 78 , 79 ], pyrrolo, pyrazolo, or imidazo-modified L -nucleoside [ 80 ], et al There have also been many methods developed to efficiently synthesize carbocyclic L -nucleoside analogues [ 52 , 81 , 82 , 83 ], and they have been summarized elsewhere [ 84 , 85 ].…”

Section: Nucleoside Analogs As Therapeutic Antiviral and Antitumor Agentsmentioning

confidence: 99%

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Advances in Therapeutic L-Nucleosides and L-Nucleic Acids with Unusual Handedness

Dantsu

Zhang

2021

Genes

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Nucleic-acid-based small molecule and oligonucleotide therapies are attractive topics due to their potential for effective target of disease-related modules and specific control of disease gene expression. As the non-naturally occurring biomolecules, modified DNA/RNA nucleoside and oligonucleotide analogues composed of L-(deoxy)riboses, have been designed and applied as innovative therapeutics with superior plasma stability, weakened cytotoxicity, and inexistent immunogenicity. Although all the chiral centers in the backbone are mirror converted from the natural D-nucleic acids, L-nucleic acids are equipped with the same nucleobases (A, G, C and U or T), which are critical to maintain the programmability and form adaptable tertiary structures for target binding. The types of L-nucleic acid drugs are increasingly varied, from chemically modified nucleoside analogues that interact with pathogenic polymerases to nanoparticles containing hundreds of repeating L-nucleotides that circulate durably in vivo. This article mainly reviews three different aspects of L-nucleic acid therapies, including pharmacological L-nucleosides, Spiegelmers as specific target-binding aptamers, and L-nanostructures as effective drug-delivery devices.

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Section: Nucleoside Analogs As Therapeutic Antiviral and Antitumor Agentsmentioning

confidence: 99%

Section: Nucleoside Analogs As Therapeutic Antiviral and Antitumor Agentsmentioning

confidence: 99%

Advances in Therapeutic L-Nucleosides and L-Nucleic Acids with Unusual Handedness

Dantsu

Zhang

2021

Genes

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“…Overall, due to the observed rapid clearance and reduced bioavailability of BCX-3040, it was concluded to be a poorer PNP inhibitor candidate in comparison to 4. [29], and possess chemotherapeutic activity [30,31]. Furthermore, the thioaminal moiety within 4 -thiofuranosyl nucleosides has been proven to be resistant to metabolic hydrolysis in comparison to native 4 -oxa analogues [32].…”

Section: Thionucleosidesmentioning

confidence: 99%

Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues

et al. 2020

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Nucleoside analogues have proven to be highly successful chemotherapeutic agents in the treatment of a wide variety of cancers. Several such compounds, including gemcitabine and cytarabine, are the go-to option in first-line treatments. However, these materials do have limitations and the development of next generation compounds remains a topic of significant interest and necessity. Herein, we discuss recent advances in the chemical synthesis and biological evaluation of nucleoside analogues as potential anticancer agents. Focus is paid to 4′-heteroatom substitution of the furanose oxygen, 2′-, 3′-, 4′- and 5′-position ring modifications and the development of new prodrug strategies for these materials.

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“…4'-Thionucleoside analogs are synthesized from intermediate 6 which, in turn, is prepared by a five-step sequence starting from methyl -D-lyxopyranoside[3]. Both pyrimidine and purine nucleosides 7 and 8 are prepared (Scheme 3) and all of them have been tested for their antitumor activity, only moderate activity being found against HTB14 human glioma cells (41.5 -83.3 μM).…”

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confidence: 99%

Heterocyclic Nucleosides: Chemical Synthesis and Biological Properties

Merino

2006

CMC

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This update covers the literature for 2002 and 2003 dealing with the main topic of the previous review entitled Heterocyclic nucleosides. Chemical synthesis and biological properties and published in Curr. Med. Chem.-AIA, 2002, 1, 389. As in the first review, the papers in this survey are grouped by the type of the heterocyclic system that acts as a spacer between the hydroxymethyl group and the base moiety.

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Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties

Cited by 13 publications

References 19 publications

Advances in Therapeutic L-Nucleosides and L-Nucleic Acids with Unusual Handedness

Advances in Therapeutic L-Nucleosides and L-Nucleic Acids with Unusual Handedness

Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues

Heterocyclic Nucleosides: Chemical Synthesis and Biological Properties

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