Bioactive fused heterocycles: Nucleoside analogs with an additional ring

Jahnz‐Wechmann, Zofia; Framski, Grzegorz; Januszczyk, Piotr; Boryski, Jerzy

doi:10.1016/j.ejmech.2014.12.026

Cited by 49 publications

(45 citation statements)

References 85 publications

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“…The most unstable analogs, equipped with 6-phenyl, substituted with electron donating groups, are the most active ones, reaching the level of activity of the parent nucleosidic drugs. Biological activity of the etheno acyclonucleosides has been described and discussed in our recent review (Jahnz-Wechmann et al, 2015 ), and in the previous review articles (Golankiewicz and Ostrowski, 2006 ; De Clercq, 2010 ).…”

Section: Application Of Etheno Compoundsmentioning

confidence: 86%

“…In the following review, we drew our attention mainly to chemistry of ethenonucleosides and related compounds. Their biological properties, fluorescence study, antiviral action, and mutagenic effect on the nucleic acid level have already been presented in other reviews or recent articles (e.g., Secrist et al, 1972 ; Steiner et al, 1973 ; Kusmierek and Singer, 1992 ; Golankiewicz and Ostrowski, 2006 ; De Clercq, 2010 ; Gómez-Bombarelli et al, 2011 ; Jahnz-Wechmann et al, 2015 ). Therefore, in this review, we will focus on the chemical properties of ethenonucleosides, barely mentioning or shortly discussing their other features.…”

Section: Introductionmentioning

confidence: 90%

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Base-Modified Nucleosides: Etheno Derivatives

et al. 2016

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This review presents synthesis and chemistry of nucleoside analogs, possessing an additional fused, heterocyclic ring of the “etheno” type, such as 1,N6-ethenoadenosine, 1,N4-ethenocytidine, 1,N2-ethenoguanosine, and other related derivatives. Formation of ethenonucleosides, in the presence of α-halocarbonyl reagents and their mechanism, stability, and degradation, reactions of substitution and transglycosylation, as well as their application in the nucleoside synthesis, have been described. Some of the discussed compounds may be applied as chemotherapeutic agents in antiviral and anticancer treatment, acting as pro-nucleosides of already known, biologically active nucleoside analogs.

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Section: Application Of Etheno Compoundsmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 90%

Base-Modified Nucleosides: Etheno Derivatives

et al. 2016

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“…Addition of a furano or pyrrolo fused ring structure to pyrimidine nucleosides transformed these compounds into fluorescent, potent antiviral agents (Carangio et al, McGuigan et al, 2001). Properties of the bicyclic, furano-pyrimidine and pyrrolo-pyrimidine, pharmacophores have been investigated mainly for deoxyribonucleoside (Carangio et al, 2001;McGuigan et al, 2001), and to lesser extent for ribonucleoside (Jahnz-Wechmann et al, 2015;Koh et al, 2007), or dideoxy derivatives (McGuigan et al, 2013). Selected examples of this type of nucleoside analogues in our investigated series included: three lipophilic pyrrolo derivatives [6-octyl-(18), 6-(2-methylbutyl)-(19), and 6-decylpyrrolo [2,3-d] Although most of the investigated compounds in this subgroup were not cytotoxic or displayed a moderate to low, not selective cytotoxicity, the 6-octylpyrol derivative 18 clearly stood out with its high selective cytotoxicity against the T98G glioblastoma cells (IC 50 = 0.74), and high selectivity index, IC 50 MRC-5/IC 50 T98G, SI = 173.…”

Section: Pyrimidine Bicyclo Nucleoside Analoguesmentioning

confidence: 99%

Searching for anti-glioma activity. Ribonucleoside analogues with modifications in nucleobase and sugar moieties.

Framski¹,

Wawrzyniak²,

Jahnz‐Wechmann³

et al. 2017

Acta Biochim Pol

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Several ribonucleoside analogues with modifications in the nucleobase and sugar moiety have been screened for anti-glioma activity in the T98G glioma cell line using cervical (HeLa) cell line as reference human malignant cells, and lung fibroblast (MCR-5) cell line as non-cancerous reference cells. Among the investigated compounds, ribonucleosides containing 6-chloropurine (3), 7-guanine (5) and a pyrrolopyrimidine (18) as nucleobases, show promising anti-glioma activity with good selectivity indices, and can be considered as lead structures for further anti-cancer studies.

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“…Tri-cyclic nucleosides and nucleotides are also utilized as dimensional probes for enzymatic studies [5,6]. Some of the tri-cyclic analogs and their derivatives reveal promising anti-viral properties [7], recently reviewed by Janz-Wechmann et al [8,9]. They are known to reveal substrate or inhibitory activities towards many enzymes of purine metabolism [2], and they are important intermediates in the process of chemical mutagenesis [10,11].…”

Section: Introductionmentioning

confidence: 99%

Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives

Stachelska-Wierzchowska

Wierzchowski

Górka

et al. 2020

Molecules

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Etheno-derivatives of 2-aminopurine, 2-aminopurine riboside, and 7-deazaadenosine (tubercidine) were prepared and purified using standard methods. 2-Aminopurine reacted with aqueous chloroacetaldehyde to give two products, both exhibiting substrate activity towards bacterial (E. coli) purine-nucleoside phosphorylase (PNP) in the reverse (synthetic) pathway. The major product of the chemical synthesis, identified as 1,N2-etheno-2-aminopurine, reacted slowly, while the second, minor, but highly fluorescent product, reacted rapidly. NMR analysis allowed identification of the minor product as N2,3-etheno-2-aminopurine, and its ribosylation product as N2,3-etheno-2-aminopurine-N2-β-d-riboside. Ribosylation of 1,N2-etheno-2-aminopurine led to analogous N2-β-d-riboside of this base. Both enzymatically produced ribosides were readily phosphorolysed by bacterial PNP to the respective bases. The reaction of 2-aminopurine-N9-β -d-riboside with chloroacetaldehyde gave one major product, clearly distinct from that obtained from the enzymatic synthesis, which was not a substrate for PNP. A tri-cyclic 7-deazaadenosine (tubercidine) derivative was prepared in an analogous way and shown to be an effective inhibitor of the E. coli, but not of the mammalian enzyme. Fluorescent complexes of amino-purine analogs with E. coli PNP were observed.

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Bioactive fused heterocycles: Nucleoside analogs with an additional ring

Cited by 49 publications

References 85 publications

Base-Modified Nucleosides: Etheno Derivatives

Base-Modified Nucleosides: Etheno Derivatives

Searching for anti-glioma activity. Ribonucleoside analogues with modifications in nucleobase and sugar moieties.

Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives

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