Synthesis and Medicinal Properties of 2-deoxyribose and ribose C-Nucleosides

Pergoli, Mauro F. A. Adamo and Roberto

doi:10.2174/138527208786786318

Cited by 36 publications

(16 citation statements)

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“…Ribose sugar is one of the most potent classes of carbohydrates due to versatile applications of its analogues ( Adamo and Pergoli, 2008 , Cappellacci et al, 2002 , Shecterle et al, 2010 ). A great deal of D-ribose and D-ribofuranose analogues are used in the synthesis of nucleoside and nucleotide derivatives ( Downey et al, 2015 , Fujisaka et al, 2019 , Komatsu and Araki, 2003 , Rahman et al, 2009 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in vivo and in silico analgesic and anti-inflammatory studies of α-D-ribofuranose derivatives

Spriha

Rahman

2021

Saudi Pharmaceutical Journal

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Section: Introductionmentioning

confidence: 99%

Synthesis, in vivo and in silico analgesic and anti-inflammatory studies of α-D-ribofuranose derivatives

Spriha

Rahman

2021

Saudi Pharmaceutical Journal

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“…In fact, they can act as C‐nucleosides where the oxygen atom of the furanose ring is replaced with a carbon atom. In addition, the replacement of P–O–C fragment with a P–C–C unit maintains the same chain length between the nucleobase and phosphorous atom of NMP …”

Section: Introductionmentioning

confidence: 99%

“…In addition, the replacement of P-O-C fragment with a P-C-C unit maintains the same chain length between the nucleobase and phosphorous atom of NMP. [15][16][17] Docking studies of the synthesized compounds were carried out using deoxycytidine kinase (dCK) which is considered responsible not only for phosphorylation of several deoxynucleosides but also numerous nucleoside analog prodrugs which are used in cancer and antiviral chemotherapy. [18] Human dCK has two subunits (homodimer) possessing 260 amino acids each, [19] and its crystal structure (1p5z.pdb, 2zia.…”

Section: Introductionmentioning

confidence: 99%

Reprofiling of full‐length phosphonated carbocyclic 2′‐oxa‐3′‐aza‐nucleosides toward antiproliferative agents: Synthesis, antiproliferative activity, and molecular docking study

et al. 2017

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A series of phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides were synthesized via 1,3 dipolar cycloaddition and evaluated for their in vitro antiproliferative activity against the growth of cancer cell lines (MCF-7, A2780, HCT116) and normal non-transformed fibroblast (MRC5) using MTT assay. Synthesized compounds exhibited antiproliferative activity in the micromolar range. Compounds 11b showed the highest activity against MCF-7 cells (IC of 0.2344 μm). Cell cycle analysis was performed for compound 11b on MCF7 cells showing arrest of cells in the S phase. Molecular docking of synthesized compounds confirmed high affinity of these compounds to two different receptors for anticancer nucleosides on dCK, namely the 1P5Z and 2ZIA, showing scores higher than the cognate ligand for all tested compounds. All synthesized compounds were evaluated according to the Lipinski, Veber, and Opera rules, and all of them passed the evaluation showing excellent features, superior to reference drugs. In addition, ADME for all the synthesized compounds was predicted through a theoretical kinetic study using the discovery studio 3.1 software.

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“…Furthermore, recently Bortolini et al described antiproliferative potential of isoxazolidines 6 [15]. Our approach to the synthesis of nucleoside analogues 7 and 8 as potential cytotoxic agents relies, besides structural similarities to the compounds with already established biological activity, on assumption that they can be considered as C-nucleoside analogues [26,27] and they contain a non-hydrolyzable C-P bond [28] through the incorporation of a diethoxyphosphoryl function at C3 into the isoxazolidine ring.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Cytotoxicity of a New Series of Isoxazolidine Based Nucleoside Analogues

Piotrowska

Cieślak

Królewska

et al. 2011

Archiv der Pharmazie

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5-Arylisoxazolidin-3-yl-3-diethoxyphosphonates have been synthesized from N-methyl-C-diethoxyphosphorylnitrone and vinyl aryls in good yields and their transformation into the respective phosphonic acids has been accomplished via dealkylation procedure using trimethylsilyl bromide. Phosphonates having 1- and 2-naphthyl substituents at C5 in the isoxazolidine ring as well as the respective phosphonic acids have been found cytotoxic to HeLa and K562 cells with IC(50) in the 0.1-0.3 mM range. Preliminary studies on mechanism of action imply that intercalation to DNA is not responsible for their cytotoxic properties.

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Synthesis and Medicinal Properties of 2-deoxyribose and ribose C-Nucleosides

Cited by 36 publications

References 0 publications

Synthesis, in vivo and in silico analgesic and anti-inflammatory studies of α-D-ribofuranose derivatives

Synthesis, in vivo and in silico analgesic and anti-inflammatory studies of α-D-ribofuranose derivatives

Reprofiling of full‐length phosphonated carbocyclic 2′‐oxa‐3′‐aza‐nucleosides toward antiproliferative agents: Synthesis, antiproliferative activity, and molecular docking study

Design, Synthesis and Cytotoxicity of a New Series of Isoxazolidine Based Nucleoside Analogues

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