Novel Carbocyclic Nucleosides Containing a Cyclobutyl Ring: Adenosine Analogues.

Hergueta, Antonio R.; Fernández, Fernando Nieto; López, Carmen; Balzarini, Jan; Clercq, Erik De

doi:10.1248/cpb.49.1174

Cited by 13 publications

(11 citation statements)

References 18 publications

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“…Nucleosides of this type are recognized by many receptors and enzymes due to their structural similarity to the natural nucleosides, however they display increased stability towards phosphorylase- and hydrolase-induced cleavage of the pseudo-glycosidic bond. Moreover, they possess a wide spectrum of biological activity, particularly, antiviral and anticancer properties [19,23,24,25,26,27,28,29,30,31,32,33]. Unfortunately, in some cases they have exhibited significant toxicity as a result of their conversion to triphosphate forms, which closely resemble natural nucleoside triphosphates (NTP), thus resulting in unwanted recognition by ATP metabolizing enzymes [34,35,36].…”

Section: Resultsmentioning

confidence: 99%

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

et al. 2018

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A series of novel 5′-norcarbocyclic derivatives of 5-alkoxymethyl or 5-alkyltriazolyl-methyl uracil were synthesized and the activity of the compounds evaluated against both Gram-positive and Gram-negative bacteria. The growth of Mycobacterium smegmatis was completely inhibited by the most active compounds at a MIC99 of 67 μg/mL (mc2155) and a MIC99 of 6.7–67 μg/mL (VKPM Ac 1339). Several compounds also showed the ability to inhibit the growth of attenuated strains of Mycobacterium tuberculosis ATCC 25177 (MIC99 28–61 μg/mL) and Mycobacterium bovis ATCC 35737 (MIC99 50–60 μg/mL), as well as two virulent strains of M. tuberculosis; a laboratory strain H37Rv (MIC99 20–50 μg/mL) and a clinical strain with multiple drug resistance MS-115 (MIC99 20–50 μg/mL). Transmission electron microscopy (TEM) evaluation of M. tuberculosis H37Rv bacterial cells treated with one of the compounds demonstrated destruction of the bacterial cell wall, suggesting that the mechanism of action for these compounds may be related to their interactions with bacteria cell walls.

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Section: Resultsmentioning

confidence: 99%

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

et al. 2018

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“…Taking into account our previous results [7,9], the literature available [17,18,19,20] regarding the activity observed for other indanyl nucleosides against different viruses, the fact that carbanucleosides derived from 2-amino-1-indanol have not been previously synthesized and evaluated as antiviral agents, and the persistent need to find effective new drugs for the treatment of hepatitis C, we decided to synthesize this type of derivative that contains triazole, purine, or azapurine moiety in their structures. Once synthesized, we evaluated their anti-HCV activity in vitro, by using the replicon cell line, Huh7.5 SG, to find new agents against this infection.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Indanyl Nucleoside Analogues and their Biological Evaluation on Hepatitis C Virus (HCV) Replicon

et al. 2019

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Here, we report a convenient synthetic procedure for the preparation of four novel indanyl carbanucleoside derivatives in the racemic form. The action of these compounds against hepatitis C virus was evaluated in vitro using the replicon cell line, Huh7.5 SG. Contrary to our expectations, all these compounds did not inhibit, but rather promoted HCV genotype 1b (HCVg1b) replication. Similar effects have been reported for morphine in the replicon cell lines, Huh7 and Huh8. Several biological experiments and computational studies were performed to elucidate the effect of these compounds on HCVg1b replication. Based on all the experiments performed, we propose that the increase in HCVg1b replication could be mediated, at least in part, by a similar mechanism to that of morphine on the enhancement of this replication. The presence of opioid receptors in Huh7.5 SG cells was indirectly determined for the first time in this work.

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“…So in recent years the synthesis and their biological activities have been studied. Many cyclobutyl analogues also have favorable bioactivities [1][2][3]. So the thiourea compounds containing cyclobutane ring may have interesting biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and crystal structure of 1-[2-(3-ethyl-2,2-dimethylcyclobutyl)acetyl]-3-phenyl thiourea

Yin¹,

Zhou²,

Yl³

et al. 2012

Bull. Chem. Soc. Eth.

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The title compound 1-[2-(3-ethyl-2,2-dimethylcyclobutyl)acetyl]-3-phenylthiourea has been synthesized and its crystal structure was studied. The crystal belongs to triclinic system, space group P-1, a = 10.200(2) Ǻ, b = 12.395(3) Å, c = 15.679(3) Å, α = 92.99(2)^o, β = 106.00(3)^o, γ = 111.95(3)^o, V = 1740.4(6) Å³, Z = 2, μ = 0.187 mm⁻¹, D_c = 1.162 g/cm³, F(000) = 656, R = 0.0784, wR2 = 0.1505, formula unit C₁₇H₂₄N₂OS. The title compound has a fragment of 2,2-dimethylcyclobutane and its conformation represents semi-chair. The intermolecular and intramolecular hydrogen bonds are revealed.DOI: http://dx.doi.org/10.4314/bcse.v27i1.1

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Novel Carbocyclic Nucleosides Containing a Cyclobutyl Ring: Adenosine Analogues.

Cited by 13 publications

References 18 publications

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

Synthesis of New Indanyl Nucleoside Analogues and their Biological Evaluation on Hepatitis C Virus (HCV) Replicon

Synthesis and crystal structure of 1-[2-(3-ethyl-2,2-dimethylcyclobutyl)acetyl]-3-phenyl thiourea

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